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A facile and stereoselective synthesis of 3,4,6-tri-O-acetyl-2-deoxy-2phthalimido-β-D-glucopyranosyl chloride.
- Source :
- Journal of Chemical Research; Aug2013, Vol. 37 Issue 8, p467-469, 3p, 2 Diagrams, 1 Chart
- Publication Year :
- 2013
-
Abstract
- Acetylation of D-glucosamine catalysed by sulfuric acid and N-phthaloylation of the glucosyl acetate yielded 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-α-D-glucopyranose. This gave the corresponding pure β-glucosyl chloride upon treatment with PCl<subscript>5</subscript>-BF<subscript>3</subscript>. An anomeric chlorination with thionyl chloride combined with the Lewis acids (ZnCl<subscript>2</subscript>, SnCl<subscript>4</subscript> and BiCl<subscript>3</subscript>) resulted in an α/β anomer mixture. [ABSTRACT FROM AUTHOR]
- Subjects :
- THALIDOMIDE
ANOMERIC effect
CHLORINATION
THIONYL chloride
LEWIS acids
Subjects
Details
- Language :
- English
- ISSN :
- 17475198
- Volume :
- 37
- Issue :
- 8
- Database :
- Complementary Index
- Journal :
- Journal of Chemical Research
- Publication Type :
- Academic Journal
- Accession number :
- 89799140
- Full Text :
- https://doi.org/10.3184/174751913X13728407114482