寡糖素的合成：丙基 O-β-D-吡喃半乳糖基-(1→2)-O-α-D-吡喃木糖基-(1→6)-O-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃葡萄糖苷的化学合成。

Synthesis of oligosaccharins: a chemical synthesis of propyl O-beta-D-galactopyranosyl-(1----2)-O-alpha-D-xylopyranosyl-(1----6)- O-beta-D-glucopyranosyl-(1----4)-beta-D-glucopyranoside.

作者信息

Wotovic A, Jacquinet J C, Sinaÿ P

机构信息

Laboratoire de Biochimie Structurale, U.R.A. 499, U.F.R.-Faculté des Sciences, Université d'Orléans, France.

出版信息

Carbohydr Res. 1990 Sep 19;205:235-45. doi: 10.1016/0008-6215(90)80143-q.

DOI:10.1016/0008-6215(90)80143-q

PMID:2276137

Abstract

Condensation of allyl 3,4-di-O-benzyl-beta-D-xylopyranoside with 2-O-acetyl-3,4,6-tri-O-benzyl-alpha-D-galactopyranosyl chloride in dichloromethane in the presence of silver triflate gave allyl 2-O-(2-O-acetyl-3,4-6-tri-O-benzyl-beta-D-galactopyranosyl)-3,4-di-O benzyl-beta-D-xylopyranoside (7, 83%). Compound 7 was converted in five steps into 2-O-(2-O-acetyl-3,4-6-tri-O-benzyl-beta-D-xylopyranosyl bromide (13), which was condensed immediately with allyl 2,3,6-tri-O-acetyl-4-O-(2,3,di-O-acetyl-beta-D-glucopyranosyl)-beta-D- glucopyranoside to give crystalline allyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-galactopyranosyl)- (1----2)-O-(3,4,-di-O-benzyl-alpha-D-xylopyranosyl)-(1----6)-O-(2,3,-di- O-acetyl-beta-D-glucopyranosyl)-(1----4)-2,3,6-tri-O-acetyl-beta-D-gluco pyranoside (23, 50%). O-Deacylation of 23 followed by catalytic hydrogenolysis gave the title glycoside.

摘要

在三氟甲磺酸银存在下，烯丙基3,4-二-O-苄基-β-D-吡喃木糖苷与2-O-乙酰基-3,4,6-三-O-苄基-α-D-吡喃半乳糖基氯在二氯甲烷中反应，得到烯丙基2-O-(2-O-乙酰基-3,4,6-三-O-苄基-β-D-吡喃半乳糖基)-3,4-二-O-苄基-β-D-吡喃木糖苷（7，产率83%）。化合物7经五步反应转化为2-O-(2-O-乙酰基-3,4,6-三-O-苄基-β-D-吡喃半乳糖基)溴化物（13），其立即与烯丙基2,3,6-三-O-乙酰基-4-O-(2,3-二-O-乙酰基-β-D-吡喃葡萄糖基)-β-D-吡喃葡萄糖苷缩合，得到结晶状的烯丙基O-(2-O-乙酰基-3,4,6-三-O-苄基-β-D-吡喃半乳糖基)-(1→2)-O-(3,4-二-O-苄基-α-D-吡喃木糖基)-(1→6)-O-(2,3-二-O-乙酰基-β-D-吡喃葡萄糖基)-(1→4)-2,3,6-三-O-乙酰基-β-D-吡喃葡萄糖苷（23，产率50%）。23进行O-脱酰基反应，随后进行催化氢解反应，得到标题糖苷。