A STEREOCHEMICALLY GENERAL-SYNTHESIS OF METHYL 2,4,6-TRIDEOXY-4-METHYLTHIO-ALPHA-D-RIBO-PYRANOSIDE, THE THIO SUGAR OF ESPERAMICIN A(1)

被引：25

作者：

ROUSH, WR

GUSTIN, D

机构：

[1] Department of Chemistry, Indiana University, Bloomington

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 28期

关键词：

D O I：

10.1016/S0040-4039(00)73285-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereochemically general synthesis of methyl 2,4,6-trideoxy-4-methylthio-alpha-D-ribo-pyranoside (1b), the thio sugar isolated from esperamicin, is described. The synthesis involves the neighboring group assisted delivery of a sulfur nucleophile to C(5) of epoxyalcohol 6 via aniline promoted cyclization of thioimidazolide 7.

引用

页码：4931 / 4934

页数：4

共 50 条

[1] SYNTHESIS OF METHYL 2,6-DIDEOXY-4-THIO-ALPHA-D-RIBO-HEXO-PYRANOSIDE, A NEW THIO SUGAR FOUND IN CALICHEMICINS
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[6] SYNTHESIS OF METHYL 2,6-DIDEOXY-4-THIO-ALPHA-D-RIBO-HEXOPYRANOSIDE (METHYL 4-THIODIGITOXOSIDE) - A CONSTITUENT OF THE CALICHEAMICINS AND ESPERAMICINS
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[7] SYNTHESIS AND ALKALINE DEGRADATION OF METHYL 2,4,6-TRI-O-METHYL-ALPHA AND 2,4,6-TRI-O-METHYL-BETA-D-RIBO-HEXOSID-3-ULOSE
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[8] H-1-NMR AND C-13-NMR STUDIES OF DERIVATIVES OF BENZYL 2-ACETAMIDO-2,6-DIDEOXY-ALPHA-D-GLUCO-PYRANOSIDE AND 2,4-DIACETAMIDO-2,4,6-TRIDEOXY-ALPHA-D-GLUCO-PYRANOSIDE AND D-GALACTO-PYRANOSIDE
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[9] PREPARATION OF METHYL 2,4-DIACETAMIDO-2,4,6-TRIDEOXY-ALPHA-D-IDOPYRANOSIDE, ALPHA-D-TALOPYRANOSIDE, ALPHA-D-ALTROPYRANOSIDE, AND ALPHA-D-MANNOPYRANOSIDE
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[10] MODEL REACTIONS UTILIZING THE CHIRAL SYNTHON, METHYL 3-0-BENZYL-2,4,6-TRIDEOXY-6-IODO-ALPHA-D-RIBO-HEXOPYRANOSIDE, IN THE SYNTHESIS OF HMG-COA REDUCTASE INHIBITORS
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