TOTAL ASYMMETRIC-SYNTHESIS OF 5-DEOXY-5-THIO-L-ALLOSE

被引：9

作者：

EMERY, F ^{[1
]}

VOGEL, P ^{[1
]}

机构：

[1] UNIV LAUSANNE,CHIM SECT,CH-1005 LAUSANNE,SWITZERLAND

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 1994年 / 13卷 / 04期

关键词：

D O I：

10.1080/07328309408011664

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：

The optically pure Diels-Alder adduct of furan to 1-cyanovinyl (1R)-camphanate was converted to methyl(methyl 5-bromo-5-deoxy-2,3-O-isopropylidene-beta-L-allo-hexo-furanosid)uronate. Ester reduction, followed by HBr elimination afforded (+)-methyl 5,6-anhydro-2,3-O-isopropylidene-D-beta-talo-hexofuranoside. Applying the method of Adley and Owen, (+)-methyl 5,6-dideoxy-5,6-epithio-2,3-O-isopropylidene-L-beta-allo-hexofuranoside was obtained and acetolysed to give, after deprotection, (-)-5-deoxy-5-thio-L-allose.

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页码：555 / 563

页数：9

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