A convenient, highly efficient one-pot preparation of peracetylated glycals from reducing sugars

Article abstract of DOI:10.1080/07328309608005701

A convenient, highly efficient, one-pot, three-step procedure has been developed for the synthesis of peracetylated glycal derivatives from various reducing sugars including D-glucose, D-galactose, L-rhamnose, L-arabinose, D-maltose, D-lactose, and maltotriose. This procedure involves peracetylation of the reducing sugars with acetic anhydride and HBr/acetic acid followed by the transformation of the anomeric acetates to the corresponding bromides with additional HBr/acetic acid and finally reductive elimination of the 1-bromo and 2-acetoxy groups with Zn/CuSC₄·5H₂O in acetic acid/water containing sodium acetate. The overall yields of purified peracetylated glycals from the corresponding sugars range from 50 - 98%.

Full text of DOI:10.1080/07328309608005701

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Journal of Carbohydrate Chemistry
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A Convenient, Highly Efficient One-Pot
Preparation of Peracetylated Glycals
From Reducing Sugars
Brian K. Shull a , Zhijun Wu a & Masato Koreeda a
a Department of Chemistry, The University of Michigan, Ann Arbor
Michigan 48109-1055, USA
Version of record first published: 19 Aug 2006
To cite this article: Brian K. Shull, Zhijun Wu & Masato Koreeda (1996): A Convenient, Highly Efficient
One-Pot Preparation of Peracetylated Glycals From Reducing Sugars, Journal of Carbohydrate
Chemistry, 15:8, 955-964
To link to this article: http://dx.doi.org/10.1080/07328309608005701
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