Glucosamine Research Today is a free monthly online journal that collates and summarizes the latest research about Glucosamine, including details on chondroitin sulfate, uses, effects, benefits, arthritis.

D-glucosamine trimethylene dithioacetal derivatives: formation of six- and seven-membered ring amino carbasugars. Synthesis of (-)-calystegine B3.

Chen YL, Redlich H, Bergander K, Fröhlich R

Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, D-48149, Münster, Germany.

By virtue of carefully chosen protecting groups, d-glucosamine trimethylene dithioacetal derivatives were successfully oxidized to the corresponding 6-aldehydes. This methodology reverses the donor and acceptor position on a normal open chain sugar and changes the relative position of the N-substituent. From the 6-aldehydes, heptose epoxide derivatives were prepared by a Corey-Chaykovsky reaction, and cyclized by the Corey-Seebach method. Depending on the designed protecting groups, the orthogonally protected six- and seven-membered ring amino carbasugars can be produced selectively and efficiently. (-)-Calystegine B(3) was synthesized from one of those products with high yield. This is the first anionic cyclization pathway to calystegine type structures.

Published 3 October 2007 in Org Biomol Chem, 5(20): 3330-9.
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