Thiosugars III. Stereoselective approach to beta-(1 -> 2)-2,3-dideoxy-2-C-acetamidomethyl-2-S-thiodisaccharides from levoglucosenone

Authors
Witczak, ZJ Chhabra, R Boryczewski, D
Citation
Zj. Witczak et al., Thiosugars III. Stereoselective approach to beta-(1 -> 2)-2,3-dideoxy-2-C-acetamidomethyl-2-S-thiodisaccharides from levoglucosenone, J CARB CHEM, 19(4-5), 2000, pp. 543-553
Citations number
32
Categorie Soggetti
Chemistry & Analysis
Journal title
JOURNAL OF CARBOHYDRATE CHEMISTRY
ISSN journal
07328303 → ACNP
Volume
19
Issue
4-5
Year of publication
2000
Pages
543 - 553
Database
ISI
SICI code
0732-8303(2000)19:4-5<543:TISATB>2.0.ZU;2-L
Abstract
beta(1-->2)-2,3-Dideoxy-2-C-acetamidomethyl-2-S-thiodisaccharides were synt hesized in four steps by a stereoselective base catalyzed Michael addition reaction of 1-thiosugars to alpha-nitroalkene 4a, a new chiral synthon from levoglucosenone. It was followed by the reduction of the nitro group with a sodium borohydride/cobalt chloride complex and the hydrolytic opening of the 1,6-anhydro ring.