JPH025762B2 - - Google Patents
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- JPH025762B2 JPH025762B2 JP14666482A JP14666482A JPH025762B2 JP H025762 B2 JPH025762 B2 JP H025762B2 JP 14666482 A JP14666482 A JP 14666482A JP 14666482 A JP14666482 A JP 14666482A JP H025762 B2 JPH025762 B2 JP H025762B2
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Description
本発明は、新規オリゴマンノシド及びその製造
法に関するものであり、更に詳細には、α1−２
結合及びα1−６結合を有する分枝状マンナン及
びその製造法に関するものである。
マンナンは高等植物から微生物まで広く分布し
ている多糖である。近年、それらの化学構造の研
究が進歩し、いくつかのくり返し単位の構造式が
提示されている。例えば、酵母マンナンがイモチ
菌のマンナンは、細胞の表層に存在しているプロ
テオマンナンであり（T.Nakajima，H.Sasaki，
M.Sato，K.Tamari and K.Matsuda，J.
Biochem.（Tokyo）82，1657〜1662）複雑に分岐
した構造が考えられている。これらのマンナン
は、表層に存在していることから生物間の認識現
象にも関与している可能性が大きい。また、いく
つかのマンナンについては、抗腫瘍活性が報告さ
れている。本発明者らは、これらの生物学的機能
や抗腫瘍活性とマンナン構造との相関の解明を目
的して、正確な構造を有するオリゴマンノシドの
合成研究を行つている。
本発明者らは、すでに、２，６−及び３，６−
分枝のマンナン構造の合成法、α1−２結合の直
鎖状マンナン構造の合成法（特願昭55−130372
号、同55−149182号、同55−149183号及び同56−
33319号明細書参照）を確立しているが、いずれ
も６糖程度であり更に、糖数の多い分枝状オリゴ
マンナン構造の合成につき鋭意研究の結果、本発
明を完成するに至つた。
以下、本発明を詳述する。
まず、出発物質は、以下の構造式を有する化合
物(1)であり、本発明者らによつてすでにマンノー
スより合成された化合物である（T.Ogawa＆K.
Sasajima Carbohydrate Research，93（1981）
67−81参照）
化合物(1)を、（CH3）3SiOSO2CF3（TMS Trif）、
SnCl4，AlCl3，PCl3，ZnCl2等のルイス酸触媒存
在下でベンジルアルコールと反応させて化合物(2)
を得る。溶媒はジクロルエタン、ジクロルメタ
ン、クロロホルム、ニトロメタン、ベンゼン、ト
ルエン等が好適である。
反応温度、反応時間は、それぞれ、約−20〜50
℃、約１分〜48時間が適当である。
得られた化合物(2)を、MeONa／MeOH，
EtONa／EtOH，ｉ−prOH／ｉ−prONa，
MeOK／KOH等のアルコラートとTHF、エーテ
ル等の溶媒中で処理して、脱アセチル化して、化
合物(3)を得る。
得られた化合物(3)を前記化合物(1)と反応させ
て、２糖化合物(4)を得るが、反応条件は、化合物
(1)→化合物(2)の反応条件と同様である。
得られた２糖化合物(4)をAgOSO2CF3，
Ag2CO3，Ag2O，AgClO4，HgBr2，Hg（CN）2
等の銀又は水銀化合物を触媒として、化合物(5)と
反応させて、３糖化合物(6)を得る。
なお、化合物(5)は、前記化合物(C)をトリメチル
ハロゲノシランと共に、還流することにより容易
に得られる（特願昭56−33319号明細書参照）。
溶媒は、ジクロルエタン、ジクロルメタン、ク
ロロホルム、ニトロメタン、ベンゼン、トルエン
等が適当であり、反応温度、反応時間は、それぞ
れ、約−20〜100℃、約１分〜48時間が適当であ
る。
この反応は、反応中生成するHBrなどの酸を
除去する目的でモレキユラー・シーブを加え反応
させるのがよい。
かくして得られた３糖化合物(6)を前記化合物(2)
→化合物(3)の反応と同様に脱アセチル化して、ト
リオール３糖化合物(7)を得る。
得られたトリオール３糖化合物(7)を前記化合物
(5)→化合物(6)の反応と同様に３分子のハロゲノ２
糖化合物(8)と反応させると保護９糖化合物(9)を得
る。
なお、ハロゲノ２糖化合物(8)は、前記化合物(A)
より、次の工程で得ることができる（特願昭56−
33319号明細書参照）。
The present invention relates to a novel oligomannoside and a method for producing the same.
The present invention relates to a branched mannan having α1-6 bonds and a method for producing the same. Mannan is a polysaccharide that is widely distributed from higher plants to microorganisms. In recent years, research on their chemical structures has progressed, and structural formulas of several repeating units have been proposed. For example, yeast mannan is a proteomannan that exists on the surface of cells (T. Nakajima, H. Sasaki,
M. Sato, K. Tamari and K. Matsuda, J.
Biochem. (Tokyo) 82, 1657-1662) A complex branched structure is considered. Since these mannans exist on the surface layer, it is highly likely that they are also involved in recognition phenomena between organisms. Furthermore, antitumor activity has been reported for some mannans. The present inventors are conducting research on the synthesis of oligomannosides having accurate structures, with the aim of elucidating the correlation between these biological functions, antitumor activities, and mannan structure. The inventors have already demonstrated that 2,6- and 3,6-
Synthesis method of branched mannan structure, method of synthesis of linear mannan structure with α1-2 bonds (Patent application No. 55-130372
No. 55-149182, No. 55-149183 and No. 56-
33319), but all of them are about hexasaccharides, and as a result of intensive research into the synthesis of branched oligomannan structures with a large number of sugars, we have completed the present invention. The present invention will be explained in detail below. First, the starting material is a compound (1) having the following structural formula, which was already synthesized from mannose by the present inventors (T. Ogawa & K.
Sasajima Carbohydrate Research, 93 (1981)
67-81) Compound (1), (CH 3 ) 3 SiOSO 2 CF 3 (TMS Trif),
Compound (2) is obtained by reacting with benzyl alcohol in the presence of a Lewis acid catalyst such as SnCl 4 , AlCl 3 , PCl 3 , ZnCl 2 etc.
get. Suitable solvents include dichloroethane, dichloromethane, chloroform, nitromethane, benzene, toluene, and the like. The reaction temperature and reaction time are approximately -20 to 50, respectively.
℃, about 1 minute to 48 hours is suitable. The obtained compound (2) was mixed with MeONa/MeOH,
EtONa/EtOH, i-prOH/i-prONa,
Compound (3) is obtained by treatment with an alcoholate such as MeOK/KOH in a solvent such as THF or ether for deacetylation. The obtained compound (3) is reacted with the above compound (1) to obtain the disaccharide compound (4), and the reaction conditions are such that the compound
The reaction conditions are the same as those for (1)→compound (2). The obtained disaccharide compound (4) was mixed with AgOSO 2 CF 3 ,
Ag 2 CO 3 , Ag 2 O, AgClO 4 , HgBr 2 , Hg(CN) 2
The trisaccharide compound (6) is obtained by reacting with the compound (5) using a silver or mercury compound such as the following as a catalyst. Compound (5) can be easily obtained by refluxing the compound (C) with trimethylhalogenosilane (see Japanese Patent Application No. 33319/1982). Suitable solvents include dichloroethane, dichloromethane, chloroform, nitromethane, benzene, toluene, etc., and suitable reaction temperatures and reaction times are approximately -20 to 100°C and approximately 1 minute to 48 hours, respectively. In this reaction, it is preferable to add a molecular sieve for the purpose of removing acids such as HBr generated during the reaction. The thus obtained trisaccharide compound (6) was converted into the above compound (2).
→ Deacetylation is performed in the same manner as the reaction of compound (3) to obtain triol trisaccharide compound (7). The obtained triol trisaccharide compound (7) was combined with the above compound
(5)→Similar to the reaction of compound (6), three molecules of halide 2
Reaction with sugar compound (8) yields protected nonasaccharide compound (9). In addition, the halogeno disaccharide compound (8) is the compound (A)
Therefore, it can be obtained by the following process (Patent application 1983-
33319)).
元素分析：C31H34O8
Ｃ Ｈ
計算値 69.95 6.41
実測値 69.90 6.41
〔α〕D：＋7.8゜（Ｃ＝1.4、CHCl3）
δH（CDCl3）：5.41（1H′q、Ｊ＝２Hz、３Hz、Ｈ−
２）
2.15（3H、ｓ、Ac）
2.09（3H、ｓ、Ac）
実施例 ２
化合物(2)1.6ｇをTHF15mlに溶解し、
0.1NMeONa／MeOH溶液15mlを加え、室温で１
時間撹拌するとtlc（トルエン：酢酸エチル＝１：
２）上で原料スポツトが消失し、新たにRf 0.37
のほぼ単一のスポツトが現われた。アンバーリス
トＡ−15で中和後、溶媒除去し、シリカゲル70ｇ
のフラツシユクロマトグラフイー（トルエン：酢
酸エチル＝１：２）で単離し、1.27ｇのシロツプ
状の化合物(3)を得た。（収率94％）
〔化合物(3)の物理的性質〕
元素分析：C27H30O6
Ｃ Ｈ
計算値 71.98 6.71
実測値 71.99 6.77
〔α〕D：＋23.5゜（Ｃ＝0.4、CHCl3）
実施例 ３
化合物(3)1.9ｇを50ml溶二口フラスコに入れ、
ジクロルエタン20mlに溶解後窒素置換した。−20
℃に冷却後TMS−OTrif 0.45mlを滴下注入し、
ジクロルエタン２ml溶の化合物(1)1.0ｇを、−20℃
で滴下注入した。０℃に昇温し、３時間撹拌した
ところ、tlc（トルエン：酢酸エチル＝２：１）上
で化合物(1)に一致するRf 0.17のスポツトと共に、
新たにRf 0.33のスポツトが現れた。反応液を重
曹水100mlにあけ、クロロホルム100mlで３回抽出
後、重曹水、飽和食塩水で洗浄し、MgSO4で脱
水した。溶媒除去後100ｇシリカゲルによるフラ
ツシユクロマトグラフイー（トルエン：酢酸エチ
ル＝２：１）により単離し、Rf 0.33のスポツト
のものを1.48ｇ、Rf 0.17のスポツトのものを930
mgそれぞれ、シロツプ状物質として得た。′Ｈ−
nmr、13C−nmrよりRf 0.33のものを化合物(4)
（収率78％）と同定した。
〔化合物(4)の物理的性質〕
元素分析：C51H56O13 Ｃ Ｈ
計算値 69.85 6.44
実測値 69.83 6.45
〔α〕D：＋20.3゜（Ｃ＝0.4、CHCl3）
δH（CDCl3）：5.55（1H、ｑ、Ｊ＝２、３Hz、Ｈ−
2b）
2.15（3H、ｓ、Ac）、
2.03（3H、ｓ、Ac）
実施例 ４
30ml褐色二口フラスコにモレキユラーシーブス
4A末３ｇ及び回転子を入れ、180℃で７時間減圧
撹拌し、室温に冷却後トルエン10ml溶の
AgSO3CF3 500mlを加え溶媒除去した。窒素置換
後ジクロルエタン15ml溶の化合物(4)600mg
（0.7mM）を注入し、室温で30分間撹拌後−15℃
に冷却し、ジクロルエタン１ml溶の化合物(5)570
mg（1.05mM）を滴下注入した。室温で２日間撹
拌した所、tlc（トルエン：酢酸エチル＝５：１）
上で原料スポツトが消失し、新たにRf 0.62のス
ポツトが現れた。
過後、溶媒除去し、シリカゲル70ｇのフラツ
シユクロマトグラフイー（トルエン：酢酸エチル
＝７：１）により単離し、600mgのシロツプ状の
化合物(6)を得た（収率65％）
〔化合物(6)の物理的性質〕
元素分析：C80H86O19 Ｃ Ｈ
計算値 71.09 6.41
実測値 70.76 6.37
〔α〕D：＋39.7゜（Ｃ＝0.4、CHCl3）
δH（CDCl3）：5.54（1H、ｑ、Ｊ＝２、３Hz、Ｈ−
2c）
5.40（1H、ｑ、Ｊ＝２、３Hz、Ｈ−2b）
2.12（6H、ｓ、Ac×２）、
2.01（3H、ｓ、Ac）
実施例 ５
化合物(6)300mgをTHF5mlに溶解し、
0.05NMeONa／MeOH溶液５mlを加えて室温で
３時間撹拌すると、tlc（トルエン：酢酸エチル＝
２：１）上で化合物(6)のスポツトが消失し、新た
にRf 0.30のスポツトが現れた。
アンバーリストＡ−15で中和後、溶媒除去し、
シリカゲル20ｇのフラツシユクロマトグラフイー
（トルエン：酢酸エチル＝２：１）により単離し
230ｇのシロツプ状の化合物(7)を得た（収率85％）
〔化合物(7)の物理的性質〕
元素分析：C74H80O16
Ｃ Ｈ
計算値 72.53 6.58
実測値 72.77 6.68
〔α〕D＝＋17.9゜（Ｃ＝0.4、CHCl3）
δH（CDCl3）：Acのシグナルが消失した。
実施例 ６
30ml容褐色二口フラスコにモレキユラーシーブ
ス5A末３ｇを入れ190℃で減圧下１晩撹拌した後
室温に冷却し、トルエン10ml溶の
AgOSO2CF3200mg（0.14mM）を注入し、40℃で
減圧下溶媒除去した。
ベンゼン10ml溶の化合物(7)150mgを注入後、室
温で30分間撹拌し、０℃に冷却後ベンゼン５ml溶
の化合物(8)300mg（0.34mM）を注入した。０℃
で30分間撹拌を続けると、tlc（トルエン：酢酸エ
チル＝１：２）上で化合物(7)及び化合物(8)のスポ
ツトがほぼ消失し、新たにRf 0.48のスポツトが
現れた。過後飽和重曹水30mlにクロロホルム30
mlと共に反応液を洗い入れ、有機層を分離後、水
層をクロロホルム30mlで２度抽出し、有機層を合
せ、水、飽和食塩水で各１回洗浄した。MgSO4
で脱水後、減圧下溶媒除去し、フラクトゲル
PVA2000（THF）で単離し、210mgの粉末状の化
合物(9)を得た。（収率56％）
〔化合物(9)の物理的性質〕
元素分析：C152H182O67
Ｃ Ｈ
計算値 59.25 5.95
実測値 59.23 6.14
〔α〕D：53.7゜（Ｃ＝0.5、CHCl3）
δH（CDCl3）：7.40−7.10（40H、ｍ、アロマチツ
ク）
2.20−1.98（63H、ｍ、21×Ac）
実施例 ７
化合物(9)150mgをTHF5mlに溶解し、
0.1NNaOMe／MeOH5mlを加え室温で３時間撹
拌するとtlc（BuOH：AcOH：H2O2：１：１）
上で、化合物(9)のスポツトが消失し、新たにRf
0.23のスポツトが現れた。アンバーリストＡ−15
で中和後、溶媒除去し、PVA2000（THF）で単
離し、80mgの粉状の化合物(10)を得た。（収率75％）
〔化合物(10)の物理的性質〕
元素分析：C110H140O46
Ｃ Ｈ
計算値 60.10 6.42
実測値 62.70 6.67
〔α〕D＝＋48.6゜（Ｃ＝2.3、MeOH）
実施例 ８
化合物(10)80mgを酢酸５mlに溶解し、10％pd−
Ｃ 200mgを加えて60℃で４時間水素添加を行う
と、tlc（BuOH：AcOH：H2O＝２：１：１）上
で原料スポツトが消失し、新たにRf 0.24のスポ
ツトが現れた。ケイ藻土過後溶媒除去し、エタ
ノールから結晶化し、水、エタノールから再結晶
化し、40mgの化合物（11）の結晶を得た。（収率
75％）
〔化合物（11）の物理的性質〕
m.p.：189℃（分解）
元素分析：C110H140O46
Ｃ Ｈ
計算値 43.90 6.28
実測値 43.95 6.19
〔α〕D：＋21.6゜（Ｃ＝0.5、水）
δC（D2O）25゜）：93.41（1a）、99.09（1b、1d）、
101.42（1c、1e、1f）、
103.03（1g、1h、1i）、
79.34（Ｃ−２×６）
δH（D2O52゜）：5.357（1a）、5.288〜5.273（1c、1e
、
1f）、5.117（1b）、5.065〜5.060（1d、1g、1h、1i）
Elemental analysis: C 31 H 34 O 8 C H Calculated value 69.95 6.41 Actual value 69.90 6.41 [α] D : +7.8° (C=1.4, CHCl 3 ) δ H (CDCl 3 ): 5.41 (1H′q, J =2Hz, 3Hz, H-
2) 2.15 (3H, s, Ac) 2.09 (3H, s, Ac) Example 2 Dissolve 1.6 g of compound (2) in 15 ml of THF,
Add 15 ml of 0.1NMeONa/MeOH solution and incubate at room temperature.
After stirring for an hour, TLC (toluene: ethyl acetate = 1:
2) The raw material spot disappears on the top, and a new Rf 0.37
Almost a single spot appeared. After neutralizing with Amberlyst A-15, remove the solvent and 70g of silica gel.
The product was isolated by flash chromatography (toluene:ethyl acetate=1:2) to obtain 1.27 g of syrupy compound (3). (Yield 94%) [Physical properties of compound (3)] Elemental analysis: C 27 H 30 O 6 C H Calculated value 71.98 6.71 Actual value 71.99 6.77 [α] D : +23.5° (C = 0.4, CHCl 3 ) Example 3 Put 1.9 g of compound (3) into a 50 ml two-necked flask,
After dissolving in 20 ml of dichloroethane, the atmosphere was replaced with nitrogen. −20
After cooling to ℃, 0.45 ml of TMS-OTrif was injected dropwise.
1.0 g of compound (1) dissolved in 2 ml of dichloroethane was heated at -20°C.
Injected dropwise. When the temperature was raised to 0°C and stirred for 3 hours, a spot of Rf 0.17 corresponding to compound (1) was observed on TLC (toluene:ethyl acetate = 2:1).
A new spot with Rf 0.33 has appeared. The reaction solution was poured into 100 ml of aqueous sodium bicarbonate, extracted three times with 100 ml of chloroform, washed with aqueous sodium bicarbonate and saturated brine, and dehydrated with MgSO 4 . After removing the solvent, they were isolated by flash chromatography using 100 g of silica gel (toluene:ethyl acetate = 2:1), and 1.48 g of the spot with Rf 0.33 and 930 g of the spot with Rf 0.17 were isolated.
mg each was obtained as a syrupy substance. 'H-
nmr, compound (4) with Rf 0.33 from 13 C−nmr
(yield 78%). [Physical properties of compound (4)] Elemental analysis: C 51 H 56 O 13 C H Calculated value 69.85 6.44 Actual value 69.83 6.45 [α] D : +20.3° (C = 0.4, CHCl 3 ) δ H (CDCl 3 ): 5.55 (1H, q, J = 2, 3Hz, H-
2b) 2.15 (3H, s, Ac), 2.03 (3H, s, Ac) Example 4 Molecular sieves in a 30ml brown two-necked flask
Add 3 g of 4A powder and a rotor, stir at 180°C under reduced pressure for 7 hours, cool to room temperature, and add 10 ml of toluene solution.
500 ml of AgSO 3 CF 3 was added and the solvent was removed. Compound (4) 600 mg dissolved in 15 ml of dichloroethane after nitrogen substitution
(0.7mM) and stirred for 30 min at room temperature -15℃.
Compound (5)570 dissolved in 1 ml of dichloroethane
mg (1.05mM) was injected dropwise. After stirring at room temperature for 2 days, TLC (toluene: ethyl acetate = 5:1)
At the top, the raw material spot disappeared and a new spot with Rf 0.62 appeared. After filtration, the solvent was removed and the product was isolated by flash chromatography (toluene:ethyl acetate = 7:1) using 70 g of silica gel to obtain 600 mg of syrup-like compound (6) (yield 65%) [Compound (6)] ) Elemental analysis: C 80 H 86 O 19 C H Calculated value 71.09 6.41 Actual value 70.76 6.37 [α] D : +39.7° (C=0.4, CHCl 3 ) δ H (CDCl 3 ): 5.54 (1H, q, J = 2, 3Hz, H-
2c) 5.40 (1H, q, J = 2, 3Hz, H-2b) 2.12 (6H, s, Ac x 2), 2.01 (3H, s, Ac) Example 5 Dissolve 300 mg of compound (6) in 5 ml of THF. ,
Add 5 ml of 0.05NMeONa/MeOH solution and stir at room temperature for 3 hours.
2:1), the spot of compound (6) disappeared, and a new spot of Rf 0.30 appeared. After neutralizing with Amberlyst A-15, remove the solvent,
Isolated by flash chromatography on 20 g of silica gel (toluene:ethyl acetate = 2:1).
230 g of syrup-like compound (7) was obtained (yield 85%) [Physical properties of compound (7)] Elemental analysis: C 74 H 80 O 16 C H Calculated value 72.53 6.58 Actual value 72.77 6.68 [α] D = +17.9° (C = 0.4, CHCl 3 ) δ H (CDCl 3 ): The Ac signal disappeared. Example 6 3 g of molecular sieves 5A powder was placed in a 30 ml brown two-necked flask, stirred overnight under reduced pressure at 190°C, cooled to room temperature, and added with 10 ml of toluene solution.
200 mg (0.14 mM) of AgOSO 2 CF 3 was injected, and the solvent was removed under reduced pressure at 40°C. After injecting 150 mg of Compound (7) dissolved in 10 ml of benzene, the mixture was stirred at room temperature for 30 minutes, cooled to 0°C, and then 300 mg (0.34 mM) of Compound (8) dissolved in 5 ml of benzene was injected. 0℃
When stirring was continued for 30 minutes, the spots of compound (7) and compound (8) almost disappeared on TLC (toluene:ethyl acetate = 1:2), and a new spot of Rf 0.48 appeared. After filtering, add 30 ml of chloroform to 30 ml of saturated sodium bicarbonate solution.
After separating the organic layer, the aqueous layer was extracted twice with 30 ml of chloroform, and the organic layers were combined and washed once each with water and saturated brine. MgSO4
After dehydration, the solvent was removed under reduced pressure and the fructogel
Isolation was performed using PVA2000 (THF) to obtain 210 mg of powdered compound (9). (Yield 56%) [Physical properties of compound (9)] Elemental analysis: C 152 H 182 O 67 C H Calculated value 59.25 5.95 Actual value 59.23 6.14 [α] D : 53.7° (C = 0.5, CHCl 3 ) δ H (CDCl 3 ): 7.40-7.10 (40H, m, aromatic) 2.20-1.98 (63H, m, 21×Ac) Example 7 150 mg of compound (9) was dissolved in 5 ml of THF,
Add 0.1NNaOMe/MeOH5ml and stir at room temperature for 3 hours to obtain tlc (BuOH:AcOH: H2O2 :1:1).
Above, the spot of compound (9) disappears and a new Rf
A spot of 0.23 appeared. Amber List A-15
After neutralization, the solvent was removed and isolated using PVA2000 (THF) to obtain 80 mg of powdered compound (10). (Yield 75%) [Physical properties of compound (10)] Elemental analysis: C 110 H 140 O 46 C H Calculated value 60.10 6.42 Actual value 62.70 6.67 [α] D = +48.6° (C = 2.3, MeOH ) Example 8 80 mg of compound (10) was dissolved in 5 ml of acetic acid, and 10% pd-
When 200 mg of C was added and hydrogenation was carried out at 60° C. for 4 hours, the raw material spot disappeared on TLC (BuOH:AcOH:H 2 O=2:1:1) and a new spot with Rf 0.24 appeared. After filtering through diatomaceous earth, the solvent was removed, crystallized from ethanol, and recrystallized from water and ethanol to obtain 40 mg of compound (11) as crystals. (yield
75%) [Physical properties of compound (11)] mp: 189℃ (decomposition) Elemental analysis: C 110 H 140 O 46 C H Calculated value 43.90 6.28 Actual value 43.95 6.19 [α] D : +21.6° (C = 0.5, water) δ C (D 2 O) 25°): 93.41 (1a), 99.09 (1b, 1d), 101.42 (1c, 1e, 1f), 103.03 (1g, 1h, 1i), 79.34 (C- 2×6) δ H (D 2 O52゜): 5.357 (1a), 5.288~5.273 (1c, 1e
,
1f), 5.117 (1b), 5.065~5.060 (1d, 1g, 1h, 1i)
Claims (1)
ル基、ベンジル基を示す。〕 で表わされる新規オリゴマンノシド。 ２ R1がベンジル基、R2がアセチル基である特
許請求の範囲第１項記載のオリゴマンノシド。 ３ R1，R2が水素原子である特許請求の範囲第
１項記載のオリゴマンノシド。 ４ 構造式： （ただし、式中、Bnはベンジル基を示す。） で表わされる化合物を、構造式 〔ただし、式中、Acはアセチル基を示す。〕 で表わされる化合物と反応させて、構造式： で表わされる化合物を得、該化合物を、構造式 （ただし、式中、Ｘはハロゲン原子を示す。） で表わされる化合物と反応させて構造式： で表わされる化合物を得、該化合物を脱アセチル
化して、構造式： で表わされる化合物を得、該化合物を、構造式： で表わされる化合物と反応せしめて、構造式： で表わされる化合物を得、該化合物を脱アセチル
化及び脱ベンジル化して、構造式： で表わされる化合物を得ることを特徴とする新規
オリゴマンノシドの製造法。 ５ 構造式： で表わされを化合物をベンジル化して、構造式： で表わされる化合物を得、該化合物を脱アセチル
化して、構造式： （ただし、式中、Bnはベンジル基を示す。） で表わされる化合物を得、該化合物を構造式 〔ただし、式中、Acはアセチル基を示す。〕 で表わされる化合物と反応させて、構造式： で表わされる化合物を得、該化合物を構造式 （ただし、式中、Ｘはハロゲン原子を示す。） で表わされる化合物と反応させて構造式： で表わされる化合物を得、該化合物を脱アセチル
化して、構造式： で表わされる化合物を得、該化合物を、構造式： で表わされる化合物と反応せしめて、構造式： で表わされる化合物を得、該化合物を脱アセチル
化及び脱ベンジル化して、構造式： で表わされる化合物を得ることを特徴とする新規
オリゴマンノシドの製造法。[Claims] 1. General formula: [However, in the formula, R 1 and R 2 represent a hydrogen atom, an acetyl group, or a benzyl group. ] A novel oligomannoside represented by. 2. The oligomannoside according to claim 1, wherein R 1 is a benzyl group and R 2 is an acetyl group. 3. The oligomannoside according to claim 1, wherein R 1 and R 2 are hydrogen atoms. 4 Structural formula: (However, in the formula, Bn represents a benzyl group.) A compound represented by the structural formula [However, in the formula, Ac represents an acetyl group. ] By reacting with a compound represented by the structural formula: A compound represented by is obtained, and the compound has the structural formula (However, in the formula, X represents a halogen atom.) By reacting with a compound represented by the structural formula: A compound represented by is obtained, and the compound is deacetylated to give the structural formula: A compound represented by is obtained, and the compound has the structural formula: By reacting with a compound represented by the structural formula: A compound represented by is obtained, and the compound is deacetylated and debenzylated to give the structural formula: A method for producing a novel oligomannoside, which is characterized by obtaining a compound represented by: 5 Structural formula: By benzylating the compound represented by, the structural formula: A compound represented by is obtained, and the compound is deacetylated to give the structural formula: (However, in the formula, Bn represents a benzyl group.) [However, in the formula, Ac represents an acetyl group. ] By reacting with a compound represented by the structural formula: A compound represented by is obtained, and the compound has the structural formula (However, in the formula, X represents a halogen atom.) By reacting with a compound represented by the structural formula: A compound represented by is obtained, and the compound is deacetylated to give the structural formula: A compound represented by is obtained, and the compound has the structural formula: By reacting with a compound represented by the structural formula: A compound represented by is obtained, and the compound is deacetylated and debenzylated to give the structural formula: A method for producing a novel oligomannoside, which is characterized by obtaining a compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14666482A JPS5936101A (en) | 1982-08-24 | 1982-08-24 | Novel oligomannoside and manufacture of the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14666482A JPS5936101A (en) | 1982-08-24 | 1982-08-24 | Novel oligomannoside and manufacture of the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5936101A JPS5936101A (en) | 1984-02-28 |
| JPH025762B2 true JPH025762B2 (en) | 1990-02-05 |
Family
ID=15412823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14666482A Granted JPS5936101A (en) | 1982-08-24 | 1982-08-24 | Novel oligomannoside and manufacture of the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5936101A (en) |
-
1982
- 1982-08-24 JP JP14666482A patent/JPS5936101A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5936101A (en) | 1984-02-28 |
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