ELECTROPHILIC ADDITION TO 4-THIO FURANOID GLYCAL - A HIGHLY STEREOSELECTIVE ENTRY TO 2'-DEOXY-4'-THIO PYRIMIDINE NUCLEOSIDES

Authors
HARAGUCHI K NISHIKAWA A SASAKURA E TANAKA H NAKAMURA K MIYASAKA T
Citation
K. Haraguchi et al., ELECTROPHILIC ADDITION TO 4-THIO FURANOID GLYCAL - A HIGHLY STEREOSELECTIVE ENTRY TO 2'-DEOXY-4'-THIO PYRIMIDINE NUCLEOSIDES, Tetrahedron letters, 39(22), 1998, pp. 3713-3716
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
22
Year of publication
1998
Pages
3713 - 3716
Database
ISI
SICI code
0040-4039(1998)39:22<3713:EAT4FG>2.0.ZU;2-V
Abstract
4-Thio furanoid glycals with different types of O-silyl protection hav e been prepared from benzyl nzyl-2-deoxy-1,4-dithio-D-erythro-pentofur anoside. Face-selectivity for PhSeCl- or N-iodosuccimide-initiated add ition of a pyrimidine base to the thioglycal was found to be controlle d by O-silyl protecting groups. Using the thioglycal protected with a 3,5-O-di-t-butylsilyl group, a highly stereoselective synthesis of bet a-2'-deoxy-4'-thio pyrimidine nucleosides has been accomplished. (C) 1 998 Elsevier Science Ltd. All rights reserved.