Synthesis of mono- and di-azido-hexopyranoses with N-alkyl and N,N-dialkyl amino groups at C-2 position: intermediates for accessing new polyaminosugars

Abstract

Michael addition reactions of morpholine and benzylamine to methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-C-phenylsulfonyl-α-D-erythro-hex-2-enopyranoside 9 furnish gluco- derivatives 10 and 11. Desulfonation at C-3 followed by synthetic manipulation produces intermediates for generating various new modified monosaccharides carrying N-alkyl and N,N-dialkyl amino groups at the C-2 position of hexopyranosides. This route also has the potential to furnish naturally occurring diaminosugars such as tobrosamine.