The synthesis of C-9 modified derivatives of the alpha-methyl glycoside ofKDN methyl ester

The synthesis of a range of C-9 substituted derivatives of the cc-methyl gl ycoside of KDN methyl ester (2) is reported. 9-Deoxy-9-iodo, 9-deoxy-9 thio acetyl and 9-azido-9-deoxy derivatives (compounds 10, 12 and 13) were all p repared from the corresponding 9-O-tosylate 8. Catalytic hydrogenation of 1 0 and 13 results in reduction to give the 9-deoxy and 9-amino-9-deoxy deriv atives 20 and 15, respectively. Further derivatisation of the amine 15 into compounds 17 and 18 was achieved via standard acylation procedures.