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
收藏
页码：661 / 675
页数：15
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