Synthesis of alditols by reductive radical fragmentation of N-phthalimido glycosides. Preparation of chiral synthetic intermediates

摘要

The reaction of N-phthalimido glycofuranosides and glycopyranosides with (Bu3SnH)-Bu-n/AIBN produces radical beta-fragmentation of the carbohydrate C1-C2 bond through the formation of anomeric alkoxy radicals. This constitutes a new two-step methodology for the facile conversion of carbohydrates into the corresponding cyclic alditols with one fewer carbon. (C) 1999 Elsevier Science Ltd. All rights reserved. [References: 15]