Vinylsulfone-modified carbohydrates: first general route to d-lividosamine (2-amino-2,3-dideoxy-d-glucose) and its new analogues

A general route to d-lividosamine and its new analogues has been devised for the first time. The essence of the present synthetic route lies in the diastereoselective introduction of N-monoalkylated and N-dialkylated amines to C-2 carbons of methyl 2,3-dideoxy-3-C-phenylsulfonyl-α-d-hex-2-enopyranoside and methyl 2,3-dideoxy-3-C-phenylsulfonyl-β-d-hex-2-enopyranoside in equatorial configurations. The 2-amino-2,3-dideoxysugrs thus generated, are desulfonated reductively at C-3 sites to produce a known intermediate for the synthesis of d-lividosamine and several new 2-N-alkylamino- and 2-N,N-dialkylamino-2,3-dideoxy analogues.