The methyl 4-O-(2,6-dideoxy-2-iodo-α-L-mannopyranosyl)-α-L-acosaminide (11) and the methyl 4-O-(2,6-dideoxy-α-L-arabinopyranosyl)-α-L-acosaminide analogue (12) have been stereoselectively synthesized in seven and eight steps, respectively, from di-O-acetyl-L-rhamnal (4) and methyl 2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside (5); the key step involved a 1,4-addition of hydrazoic acid to a corresponding hex-2-enopyranose.
B. Abbaci, J. Florent and C. Monneret, J. Chem. Soc., Chem. Commun., 1989, 1896 DOI: 10.1039/C39890001896
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