Synthetic Studies on Carbohydrate Antibiotics

Part II. Synthesis of 6-Deoxy-D-arabino-Hexofuranos-5-ulose, the Sugar Component of Hygromycin A

Abstract

Methyl2, 3, 4-tri-O-benzoyl-6-deoxy-a-D-arabino-hex-5-enopyranoside (IIIa) was synthesized starting from methyl α-D-altroside (IIa). This enose derivative (IIIa) was hydrolyzed to methyl 6-deoxy-α-D-arabino-hex-5-enopyranoside (IIIb), and then converted with acid into 6-deoxy-D-arabino-hexofuranos-5-ulose (I), the sugar component of antibiotic hygromycin A.