A Convenient, Highly Efficient One-Pot Preparation of Peracetylated Glycals From Reducing Sugars
Title:
A Convenient, Highly Efficient One-Pot Preparation of Peracetylated Glycals From Reducing Sugars
Author:
Shull, Brian K. Wu, Zhijun Koreeda, Masato
Appeared in:
Journal of carbohydrate chemistry
Paging:
Volume 15 (1996) nr. 8 pages 955-964
Year:
1996-11-01
Contents:
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/CuSO4ยท5H2O in acetic acid/water containing sodium acetate. The overall yields of purified peracetylated glycals from the corresponding sugars range from 50 - 98%.