1,6-ANHYDRO-BETA-D-GLUCOPYRANOSE IN ORGANIC-SYNTHESIS - PREPARATION OF A FRAGMENT FOR THE SYNTHESIS OF ROSARAMYCIN

被引：8

作者：

PROCTER, G ^{[1
]}

GENIN, D ^{[1
]}

CHALLENGER, S ^{[1
]}

机构：

[1] UNIV WALES COLL CARDIFF,DEPT CHEM,CARDIFF CF1 1XL,S GLAM,WALES

来源：

CARBOHYDRATE RESEARCH | 1990年 / 202卷

关键词：

D O I：

10.1016/0008-6215(90)84072-3

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：

1,6-Anhydro-β-d-glucopyranose has been used as the starting material for a synthesis of ethyl (E)-4-C-allyl-2,3,4,6-tetradeoxy-5,7-O-isopropylidene-8-O-methanesulphonyl-2,6-di-C-methyl-d-gulo-oct-2-enoate, which represents a synthetic unit equivalent to C-2/9 of the macrolide antibiotic rosaramycin. The synthesis involved a minimum of chromatography, and the extremely high level of regiochemical and stereochemical control was achieved by the use of epoxides at crucial CC-bond-forming steps. A method was also developed, using tosylmethyl isocyanide, which converted a carbohydrate 6-aldehyde (19) directly into the corresponding homologated methyl ester. © 1990.

引用

页码：81 / 92

页数：12

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