SYNTHESIS AND REACTIONS OF AN (ALPHA-D-GLUCOPYRANOSYL)PHENYLACETYLENE

被引：17

作者：

DESIRE, J ^{[1
]}

VEYRIERES, A ^{[1
]}

机构：

[1] UNIV ORLEANS,UFR FAC SCI,BIOCHIM STRUCT LAB,URA 499,F-45067 ORLEANS,FRANCE

来源：

CARBOHYDRATE RESEARCH | 1995年 / 268卷 / 02期

关键词：

SYNTHESIS; REACTIONS; (ALPHA-D-GLUCOPYRANOSYL)PHENYLACETYLENE;

D O I：

10.1016/0008-6215(94)00326-B

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：

Silver tetrafluoroborate promoted addition of (phenylethynyl)tributylstannane to 6-O-acety-1,2,3,4-tri-O-benzyl-alpha-D-glucopyranosyl chloride stereoselectively gave a crystalline (alpha-D-glucopyranosyl)phenylacetylene (4) in 73% yield. Compound 4 was epimerized to the beta isomer through its hexacarbonyldicobalt complex, and was also converted into a C-alpha-glycosyl aldehyde (8) by sequential zinc reduction and ozonolysis. The sensitive aldehyde 8 was conveniently isolated and manipulated through its 1,3-diphenylimidazolidine derivative.

引用

页码：177 / 186

页数：10

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