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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 PCl5-BF3. An anomeric chlorination with thionyl chloride combined with the Lewis acids (ZnCl2, SnCl4 and BiCl3) 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 :
- Academic Search Index
- Journal :
- Journal of Chemical Research
- Publication Type :
- Academic Journal
- Accession number :
- 89799140
- Full Text :
- https://doi.org/10.3184/174751913X13728407114482