Synthesis of methyl gentosaminide, methyl 3-deoxy-3-methylaminoarabinopyranoside, and related amino-sugars

Abstract

The synthesis of both α- and β-anomers of methyl gentosaminide (methyl 3-deoxy-3-methylamino-D-xylopyranoside), a component of the amino-glycoside antibiotics gentamicin A and 66-40B, is described. A number of novel 3-alkylamino-analogues of gentosamine have been prepared and the synthesis of the L-enantiomer is also discussed. The preparation of methyl 3-deoxy-3-methylamino-α-D-arabinopyranoside and of the L-enantiomer, involving use of novel epoxy-ketone intermediates, is described. The L-enantiomer has recently been demonstrated to be a component of the amino-glycoside antibiotics 66-40D and gentamicins A₁, A₃, and B₂.