Synthesis of the Antibiotic 1,5-dideoxy-1,5-imino-d-mannitol

1 September 1988

journal article
research article
Published by Taylor & Francis in Journal of Carbohydrate Chemistry

Vol. 7 (3) , 593-603
https://doi.org/10.1080/07328308808057553

Abstract

Easily accessible benzyl 2,3-O-isopropylidene-α-D-mannofuranoside (1) was converted in six steps into benzyl 2,3-O-isopropylidene-5-N-benzyl-5-deoxy-6-O-benzyl-α-D-mannofuranoside or benzyl 2,3-O-isopropylidene-5-azido-5-deoxy-6-O-benzyl-α-D-mannofuranoside. Both compounds afforded, after hydrogenolysis and acidolysis, 1-deoxymannojirimycin in an overall yield of 38% based on 1.

This publication has 1 reference indexed in Scilit:

Synthesis of 5-amino-5-deoxy-d-mannopyranose and 1,5-di-deoxy-1,5-imino-d-mannitol, and inhibition of α- and β-d-mannosidases
Carbohydrate Research, 1984