Abstract
Lithium aluminum hydride reduction of 6-azido-3-O-benzyl-6-deoxy-1, 2-O-isopropylidene-β-L-idofuranose (5b) afforded 3-O-benzyl-5, 6-dideoxy-5, 6-epimino-1, 2-O-isopropylidene-α-D-glucofuranose (1a). Its acetate (1b) was treated with acetic acid to give an 5-acetamido-6-O-acetyl-5-deoxy-derivative (6) which was transformed into a monosaccharide antibiotic, nojirimycin (2) which was produced by some strains of Streptomyces and showed activity against Sarcina lutea and Xanthomonas oryzae.
