α-L-鼠李糖吡喃糖苷甲基二-O-糖基衍生物的合成
Synthesis of di-O-glycosyl derivatives of methyl alpha-L-rhamnopyranoside.
作者信息
Nifant'ev N E, Lipkind G M, Shashkov A S, Kochetkov N K
机构信息
N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the U.S.S.R., Moscow.
出版信息
Carbohydr Res. 1992 Jan;223:109-28. doi: 10.1016/0008-6215(92)80010-x.
The syntheses are described of 2,3-di-O-glycosyl derivatives (1-12) of methyl alpha-L-rhamnopyranoside where the glycosyl moieties are variously alpha-L-fucopyranose, beta-L-fucopyranose, beta-D-glucopyranose, alpha-D-mannopyranose, and alpha-L-rhamnopyranose. The syntheses involve stereoselective glycosylation of methyl 4-O-benzoyl-3-O-(2,3,4-tri-O-benzoyl-alpha-L- rhamnopyranosyl)-alpha-L-rhamnopyranoside (21), methyl 4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl)- alpha-L-rhamnopyranoside (25), methyl 4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl)- alpha-L-rhamnopyranoside (29), methyl 4-O-benzoyl-3-O-(2,3,4-tri-O-benzoyl-beta-L-fucopyranosyl)-alpha-L- rhamnopyranoside (35), and methyl 4-O-benzyl-2-O-(2,3,4-tri-O-benzoyl-beta-L-fucopyranosyl)- alpha-L-rhamnopyranoside (59). In the syntheses of compounds 7-9, the alpha-L-fucopyranosyl residues are introduced stereoselectively, using 2,3,4-tri-O-benzoyl-alpha-L-fucopyranosyl bromide (17) and ethyl 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranoside (47) as glycosyl donors.
描述了α-L-鼠李吡喃糖苷甲基酯的2,3-二-O-糖基衍生物（1-12）的合成，其中糖基部分分别为α-L-岩藻吡喃糖、β-L-岩藻吡喃糖、β-D-葡萄糖吡喃糖、α-D-甘露吡喃糖和α-L-鼠李吡喃糖。合成过程涉及4-O-苯甲酰基-3-O-（2,3,4-三-O-苯甲酰基-α-L-鼠李吡喃糖基）-α-L-鼠李吡喃糖苷甲基酯（21）、4-O-苯甲酰基-3-O-（2,3,4,6-四-O-苯甲酰基-α-D-甘露吡喃糖基）-α-L-鼠李吡喃糖苷甲基酯（25）、4-O-苯甲酰基-3-O-（2,3,4,6-四-O-苯甲酰基-β-D-葡萄糖吡喃糖基）-α-L-鼠李吡喃糖苷甲基酯（29）、4-O-苯甲酰基-3-O-（2,3,4-三-O-苯甲酰基-β-L-岩藻吡喃糖基）-α-L-鼠李吡喃糖苷甲基酯（35）和4-O-苄基-2-O-（2,3,4-三-O-苯甲酰基-β-L-岩藻吡喃糖基）-α-L-鼠李吡喃糖苷甲基酯（59）的立体选择性糖基化。在化合物7-9的合成中，使用2,3,4-三-O-苯甲酰基-α-L-岩藻吡喃糖基溴（17）和2,3,4-三-O-乙酰基-1-硫代-β-L-岩藻吡喃糖苷乙酯（47）作为糖基供体，立体选择性地引入α-L-岩藻吡喃糖基残基。
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