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

Authors
ROUSH WR GUSTIN D
Citation
Wr. Roush et D. Gustin, A STEREOCHEMICALLY GENERAL-SYNTHESIS OF METHYL 4,6-TRIDEOXY-4-METHYLTHIO-ALPHA-D-RIBO-PYRANOSIDE, THE THIO SUGAR OF ESPERAMICIN A(1), Tetrahedron letters, 35(28), 1994, pp. 4931-4934
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
28
Year of publication
1994
Pages
4931 - 4934
Database
ISI
SICI code
0040-4039(1994)35:28<4931:ASGOM4>2.0.ZU;2-Q
Abstract
A stereochemically general synthesis of methyl ,4,6-trideoxy-4-methylt hio-alpha-D-ribo-pyranoside (1b), the thio sugar isolated from esperam icin, is described. The synthesis involves the neighboring group assis ted delivery of a sulfur nucleophile to C(5) of epoxyalcohol 6 via ani line promoted cyclization of thioimidazolide 7.