Glycosidation of 3,4,6-tri-O-benzyl-2-ethenyl-D-glucal -: A route to 2-C-(β-methyl)methylene glycosides

被引：7

作者：

Feit, BA ^{[1
]}

Kelson, IK

Gerull, A

Abramson, S

Schmidt, RR

机构：

[1] Tel Aviv Univ, Raymond & Beverly Sackler Fac Exact Sci, Sch Chem, IL-69978 Tel Aviv, Israel

[2] Univ Konstanz, Fac Chem, D-7750 Constance, Germany

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2000年 / 19卷 / 06期

关键词：

D O I：

10.1080/07328300008544109

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：

Monosaccharidic and disaccharidic 2-C-(beta-methyl)methylene glycosides were synthesized by an electrophilic conjugate addition reaction of ROH-type compounds in the presence of Ph3+PH Br- to 2-ethenyl-3,4,6-tri-O-benzyl-D-glucal 1, functioning as a model glycosyl donor. This 2-vinyl glucal derivative represents a series of 2-vinyl, and 2-butadienyl glycals, prepared by Wittig-type methylenation of pyranosidic conjugated enals, derived from glucal, galactal and lactal. The exo-(beta-methyl)methylene group paves the way for further chemical transformations.

引用

页码：661 / 675

页数：15

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