THIOSUGARS .2. A NOVEL-APPROACH TO THIODISACCHARIDES - THE SYNTHESIS OF 3-DEOXY-4-THIOCELLOBIOSE FROM LEVOGLUCOSENONE

Authors
WITCZAK ZJ CHHABRA R CHEN H XIE XQ
Citation
Zj. Witczak et al., THIOSUGARS .2. A NOVEL-APPROACH TO THIODISACCHARIDES - THE SYNTHESIS OF 3-DEOXY-4-THIOCELLOBIOSE FROM LEVOGLUCOSENONE, Carbohydrate research, 301(3-4), 1997, pp. 167-175
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Carbohydrate research → ACNP
ISSN journal
00086215
Volume
301
Issue
3-4
Year of publication
1997
Pages
167 - 175
Database
ISI
SICI code
0008-6215(1997)301:3-4<167:T.ANTT>2.0.ZU;2-Q
Abstract
An expeditious methodology for the synthesis of beta-(1 --> 4)-3-deoxy thiodisaccharides (3-deoxythiocellobiose) has been developed. The meth odology is based on the stereoselective Michael addition of 2,3,4,6-te tra-O-acetyl-1-thio-beta-D-glucose to levoglucosenone, followed by ste reoselective reduction at C-2 with L-Selectride(R) and DIBAH, followed by acetolysis to the target thiodisaccharide derivative. (C) 1997 Els evier Science Ltd.