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Organic Chemistry

Synthetic Studies on Carbohydrate Antibiotics

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

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Pages 1079-1085 | Received 31 May 1967, Published online: 09 Sep 2014
 

Abstract

New synthetic methods for the preparation of 6-deoxy-1,2-O-isopropylidene-α-d-xylo-hexofuranos-5-ulse (VIa) were described.

Methyl 2,3,4-tri-O-benzoyl-6-deoxy-α-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.

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