2-(dimethyl (2-naphthylmethyl)silyl) ethoxy carbonate (NSEC) as a new mode of hydroxyl group protection

被引：5

作者：

Bufali, S ^{[1
]}

Hölemann, A ^{[1
]}

Seeberger, PH ^{[1
]}

机构：

[1] ETH, Organ Chem Lab, CH-8092 Zurich, Switzerland

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2005年 / 24卷 / 4-6期

关键词：

carbonate; carbohydrates; deprotection; glycosylation; oligosaccharides; silyl protecting group;

D O I：

10.1081/CAR-200067008

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

2-[Dimethyl(2-naphthylmethyl)silyl]ethoxy carbonate (NSEC) is a novel protecting group to mask hydroxyl groups. NSECCl is available in three steps from chlorodimethyl-vinylsilane and 2-(bromomethyl)naphthalene. Introduction and removal of the NSEC group are performed easily and rapidly in the presence of most protecting groups currently used in carbohydrate chemistry. The removal of NSEC can be carried out under mild conditions in the presence of various ether and ester protecting groups. Additionally, the NSEC group is stable to glycosylation conditions using glycosyl phosphates. The synthesis of disaccharide 18 containing NSEC has been accomplished.

引用

页码：441 / 462

页数：22

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