A NOVEL ALDOL-TYPE C-GLYCOSIDATION REACTION PROMOTED BY SAMARIUM DIIODIDE - REGIOSELECTIVE GENERATION OF A ULOSE-1-ENOLATE FROM PHENYL BENZYL-1-THIO-BETA-D-ARABINO-HEXOPYRANOSID-2-ULOSE

Authors
ICHIKAWA S SHUTO S MATSUDA A
Citation
S. Ichikawa et al., A NOVEL ALDOL-TYPE C-GLYCOSIDATION REACTION PROMOTED BY SAMARIUM DIIODIDE - REGIOSELECTIVE GENERATION OF A ULOSE-1-ENOLATE FROM PHENYL BENZYL-1-THIO-BETA-D-ARABINO-HEXOPYRANOSID-2-ULOSE, Tetrahedron letters, 39(25), 1998, pp. 4525-4528
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
25
Year of publication
1998
Pages
4525 - 4528
Database
ISI
SICI code
0040-4039(1998)39:25<4525:ANACRP>2.0.ZU;2-B
Abstract
A novel aldol-type C-glycosidation reaction promoted by samarium diiod ide (Sml(2)) was developed. Treatment of phenyl benzyl-1-thio-beta-D-a rabino-hexopyranosid-2-ulose (6) with SmI2 in THF regioselectively gav e the corresponding 1-enolate, which was readily trapped with ketones or aldehydes to afford various C-glycosides in high yields. (C) 1998 E lsevier Science Ltd. All rights reserved.