Synthesis of 4,4-difluoroglycosides using ring-closing metathesis

被引：41

作者：

Audouard, C

Fawcett, J

Griffiths, GA

Percy, JM

Pintat, S

Smith, CA

机构：

[1] Univ Leicester, Dept Chem, Leicester LE1 7RH, Leics, England

[2] GlaxoSmithKline Pharmaceut, Harlow CM19 5AW, Essex, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2004年 / 2卷 / 04期

关键词：

D O I：

10.1039/b313731g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Deoxy-4,4-difluoro-glycosides have been synthesised for the first time via a direct sequence involving ring-closing metathesis and indium-mediated difluoroallylation with 1-bromo-1,1-difluoropropene in water. Two protecting group strategies were explored, one to allow protection of the primary C-6 hydroxyl group throughout the sequence, while the second was intended to allow deprotection after RCM and before dihydroxylation. The benzyl ether could be used in the first role, and pivaloyl is effective in the second. Dihydroxylations were highly stereoselective and controlled by the orientation of the glycosidic C-O bond.

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页码：528 / 541

页数：14

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