Convenient Approaches To Synthesis Of Furanoid Sugar-Aza-Crown Ethers From C-Ribosyl Azido Aldehyde Via A Reductive Amination/Amidation

A short and highly efficient route to the alpha-anomer of a furanoid sugar-aza-crown ether was developed by a one-pot reductive amination of an alpha-anomer C-ribosyl azido aldehyde. In addition, the beta-anomer furanoid sugar-aza-crown ether was synthesized from a linear disaccharide precursor via amidation and then followed by microwave-assisted amide reduction. (C) 2009 Elsevier Ltd. All rights reserved.