Synthesis of methyl 2-O-allyl-( and 3-O-allyl-) 5-O-benzyl-beta-D-ribofuranoside

被引：10

作者：

Desai, T ^{[1
]}

Gigg, J ^{[1
]}

Gigg, R ^{[1
]}

机构：

[1] NATL INST MED RES,DIV LIPID & GEN CHEM,LONDON NW7 1AA,ENGLAND

来源：

CARBOHYDRATE RESEARCH | 1996年 / 280卷 / 02期

关键词：

allyl ethers; methyl; 3-O-allyl-5-O-benzyl-beta-D-ribofuranoside; 2-O-allyl-5-O-benzyl-beta-D-ribofuranoside; 'adenophostin' analogue; inositol trisphosphate receptor; 'glucositol trisphosphate';

D O I：

10.1016/0008-6215(95)00308-8

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：

D-Ribose was converted into methyl 5-O-benzyl-beta-D-ribofuranoside and this, on tin-mediated allylation, gave a mixture of the 2-O-allyl and 3-O-allyl derivatives which were separated by chromatography. The more polar isomer was characterised as the 3-O-allyl derivative after conversion via 3-O-allyl-5-O-benzyl-1,2-O-isopropylidene-alpha-D-ribofuranose (which was also synthesised from 3-O-allyl-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose) into the known 5-O-benzyl-1,2-O-isopropylidene-alpha-D-ribofuranose. Methyl 3-O-allyl-5-O-benzyl-beta-D-ribofuranoside was converted into methyl 2-O-allyl-5-O-benzyl-beta-D-ribofilranoside via methyl 2-O-allyl-5-O-benzyl-3-O-(prop-1-enyl)-beta-D-ribofuranoside.

引用

页码：209 / 221

页数：13

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