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Abstract
Oxidation of methyl α- and β- d-galactopyranoside with periodic acid in dimethyl sulphoxide gave, in each case, one major, monomeric product, isolated as a diacetate. These syrupy products were characterised by m.s. and 1H- and 13C-n.m.r. spectroscopy as (1 S,2 S,4 R,7 S)-7-acetoxy-4-acetoxymethyl-2-methoxy-3,6,8-trioxabicyclo[3.2.1.]octane and (1 S,2 R,4 R,7 S)-7-acetoxy-4-acetoxymethyl-2-methoxy-3,6,8-trioxabicyclo[3.2.1.]octane, respectively. Chemical shifts and coupling constants for the products were determined partly from the experimental n.m.r. spectra, and partly by an iterative fitting-procedure with the computer program NEMEN.
Published Version
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