一种适当保护的核心糖四糖苷的合成，糖蛋白“双叉”复合型聚糖合成的关键中间体。

Synthesis of an appropriately protected core glycotetraoside, a key intermediate for the synthesis of "bisected" complex-type glycans of a glycoprotein.

作者信息

Yamazaki F, Kitajima T, Nukada T, Ito Y, Ogawa T

机构信息

Riken (The Institute of Physical and Chemical Research), Saitama, Japan.

出版信息

Carbohydr Res. 1990 Jun 15;201(1):15-30. doi: 10.1016/0008-6215(90)84222-g.

DOI:10.1016/0008-6215(90)84222-g

PMID:2208189

Abstract

A stereocontrolled synthetic route to a glycotetraoside, allyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1--- -4)-O- (3,6-di-O-allyl-2-O-benzyl-beta-D-mannopyranosyl)-(1----4)-O-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4)-3-O- benzyl- 2-deoxy-6-O-p-methoxy-phenyl-2-phthalimido-beta-D-glucopyranoside, an important intermediate for the synthesis of "bisected" complex type glycans of glycoproteins has been established by employing two glycosyl donors, 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate and 4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-alpha-D-mannopyranosyl bromide, and a glycosyl acceptor, allyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4) -3-O- benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-beta-D-glucopyranoside.

摘要

已通过使用两种糖基供体，即3,4,6-三-O-苄基-2-脱氧-2-邻苯二甲酰亚胺基-β-D-吡喃葡萄糖基三氯乙酰亚胺酯和4-O-乙酰基-3,6-二-O-烯丙基-2-O-苄基-α-D-甘露吡喃糖基溴化物，以及一种糖基受体，烯丙基O-(3,6-二-O-苄基-2-脱氧-2-邻苯二甲酰亚胺基-β-D-吡喃葡萄糖基)-(1→4)-3-O-苄基-2-脱氧-6-O-对甲氧基苯基-2-邻苯二甲酰亚胺基-β-D-吡喃葡萄糖苷，建立了一条立体控制的合成路线，用于合成糖四糖苷烯丙基O-(3,4,6-三-O-苄基-2-脱氧-2-邻苯二甲酰亚胺基-β-D-吡喃葡萄糖基)-(1→4)-O-(3,6-二-O-烯丙基-2-O-苄基-β-D-甘露吡喃糖基)-(1→4)-O-(3,6-二-O-苄基-2-脱氧-2-邻苯二甲酰亚胺基-β-D-吡喃葡萄糖基)-(1→4)-3-O-苄基-2-脱氧-6-O-对甲氧基苯基-2-邻苯二甲酰亚胺基-β-D-吡喃葡萄糖苷，这是合成糖蛋白“二分”复合型聚糖的重要中间体。