Isothiocyanato derivatives of sugars in the stereoselective synthesis of spironucleosides and spiro-C-glycosides

Authors
Gasch, C Pradera, MA Salameh, BAB Molina, JL Fuentes, J
Citation
C. Gasch et al., Isothiocyanato derivatives of sugars in the stereoselective synthesis of spironucleosides and spiro-C-glycosides, TETRAHEDR-A, 12(9), 2001, pp. 1267-1277
Citations number
58
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
9
Year of publication
2001
Pages
1267 - 1277
Database
ISI
SICI code
0957-4166(20010611)12:9<1267:IDOSIT>2.0.ZU;2-K
Abstract
A stereocontrolled synthesis of pyranoid and furanoid spironucleosides and spiro-C-glycosides (D-ribo and D-arabino configurations) of oxazolidines, o xazolines and perhydrooxazines via isothiocyanato sugar derivatives is repo rted. The intermediate isothiocyanates are prepared from sugar spiroketals by stereoselective opening of the acetal ring with trimethylsilyl N- and C- nucleophiles, and later formation of the isothiocyanato group. (C) 2001 Els evier Science Ltd. All rights reserved.