A Facile and Stereoselective Synthesis of 3,4,6-Tri- O -Acetyl-2-Deoxy-2-Phthalimido-β-D-Glucopyranosyl Chloride

A Facile and Stereoselective Synthesis of 3,4,6-Tri- O -Acetyl-2-Deoxy-2-Phthalimido-β-D-Glucopyranosyl Chloride

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 5 -BF 3 . An anomeric chlorination with thionyl c...

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Veröffentlicht in:Journal of chemical research 2013-08, Vol.37 (8), p.467-469
Hauptverfasser: Cao, Zhiling, Liu, Wenjie, Qu, Yingying, Yao, Guowei, Gao, Dachao, Liu, Weiwei
Format: Artikel
Sprache:eng
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Zusammenfassung: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 5 -BF 3 . An anomeric chlorination with thionyl chloride combined with the Lewis acids (ZnCl 2 , SnCl 4 and BiCl 3 ) resulted in an α/β anomer mixture.
ISSN:1747-5198
2047-6507
DOI:10.3184/174751913X13728407114482