Joined use of oxazolidinone and desymmetric amino protection: a new strategy for protection of glucosamine

Abstract

Joined use of N-benzyl oxazolidinone and N-benzyl-N-benzyloxycarbonyl (N-BnCbz) desymmetric amino-protecting function is reported. The new synthetic approach enables the facile preparation of type I and type 2 LacNAc disaccharides in satisfactory yields. One-pot deprotection of N-BnCbz and O-benzyl ether is achieved by hydrogenolysis under mild conditions. (C) 2010 Elsevier Ltd. All rights reserved.