Facile separation of chiral 1,3-dihydrobenzo[c]furan derivatives using a D-xylose moiety as a protecting group

被引：27

作者：

Ewing, DF

Len, C ^{[1
]}

Mackenzie, G

Ronco, G

Villa, P

机构：

[1] Univ Hull, Dept Chem, Hull HU6 7RX, N Humberside, England

[2] Univ Picardie, Lab Glucides, F-80039 Amiens, France

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 24期

关键词：

D O I：

10.1016/S0957-4166(00)00488-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

1,2-O-Isopropylidene-alpha -D-xylofuranose has been used to protect one aldehyde group of o-phthalaldehyde. This chiral protecting group acts as a resolving agent and this leads to separable diastereoisomers when a new stereogenic centre is created by the conversion of the second aldehyde group to a benzyloxyhydroxyethyl chain. These separated diastereoisomers were cyclised to 1,3-dihydrobenzo[c]furans with retention of chiral integrity at the C3 site thus allowing further elaboration to enantiomerically pure nucleoside analogues. (C) 2001 Published by Elsevier Science Ltd.

引用

页码：4995 / 5002

页数：8

共 21 条

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[2]

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