Abstract
The N-imidazolylsulfonyl derivatives of methyl 3- O-benzyl-4,6- O-benzylidene-α- d-mannopyranoside, methyl 3,4,6-tri- O-benzyl-α- d-mannopyranoside, a lactose derivative 10 protected everywhere except at OH-2′, benzyl 6- O-allyl-3,4- O-isopropylidene- α- d-galactopyranoside, and methyl 3,4,6-tri- O-methyl-β- d-galactopyranoside were prepared. Reactions of the manno derivatives with azide in toluene solution gave a moderate yield of the gluco azides 3 and 6, probably because of the prevalence of trans-elimination. A normal substitution product was obtained with one of the galacto derivatives, namely benzyl 6- O-allyl-2-azido-2-deoxy-3,4- O-isopropylidene- α- d-talopyranoside, a precursor of benzyl 2-acetamido-2-deoxy-α- d-talopyranoside. However, the main reaction was always a ring contraction with C-1 substitution, leading to the epimeric pairs 12, 13; 14, 15; 26, 27; and 32, 33.
Published Version
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