SYNTHESIS OF 3-SUBSTITUTED (AZIDO, ACYLTHIO, CHLORO OR FLUORO)-2,3-DIDEOXY-D-ERYTHRO-PENTOSES AND ETHYL-3-SUBSTITUTED-2,3-DIDEOXY-D-ERYTHRO-PENTOSES

Authors
RAIFELD YE NIKITENKO AA ARSHAVA BM MIKERIN IE ZILBERG LL VID GY LANG SA LEE VJ
Citation
Ye. Raifeld et al., SYNTHESIS OF 3-SUBSTITUTED (AZIDO, ACYLTHIO, CHLORO OR FLUORO)-2,3-DIDEOXY-D-ERYTHRO-PENTOSES AND ETHYL-3-SUBSTITUTED-2,3-DIDEOXY-D-ERYTHRO-PENTOSES, Tetrahedron, 50(29), 1994, pp. 8603-8616
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
29
Year of publication
1994
Pages
8603 - 8616
Database
ISI
SICI code
0040-4020(1994)50:29<8603:SO3(AC>2.0.ZU;2-S
Abstract
The enantioselective synthesis of 3-substituted and 3-methyl-3-substit uted 2,3-dideoxy-D-erythro-pentoses from (3R,4R)-1,1-diethoxy-3,4-epox ypentane-5-ol, 3R,4R)-1,1-diethoxy-3,4-epoxy-3-methylpentane-5-ol and (2R,3R)-2,3-epoxy-5-hexen-1-ol is reported. The key step is cleavage o f the oxirane ring by Ti(O-i-Pr)(3)X class reagents followed by select ive cyclization of the acyclic acetals to the furanosides. Fluorinatio n with the complex of titanium (IV) iso-propoxide - titanium (IV) fluo ride provides an enantioselective synthesis of 3-fluoro-2,3-dideoxy-D- erythro-pentose and 3-fluoro-3-methyl-2,3-dedeoxy-D-erythro-pentose.