Process for producing acosamine, daunosamine, 1-thioacosamine an

Details Process for producing acosamine, daunosamine, 1-thioacosamine an Process for producing acosamine, daunosamine, 1-thioacosamine an

1981-04-06

1983-11-01

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 172, 536 175, 536 185, 536 553, 536 64, C07H 100

Patent

active

044131208

ABSTRACT:
A process for synthesizing acosamine, daunosamine and 1-thioacosamines from L-rhamnal is disclosed that can generally be characterized by Michael addition of an alkoxide or thioalkoxide to the enone formed by allylic oxidation of L-rhamnal to directly generate the 2-deoxy functionality, and stereospecific reduction of the oxime to the arabino compound which establishes configuration at C-3 and generates a compound which requires only epirmerization at C-4 to yield the desired product. The synthesis of anthracycline antibiotics incorporating these sugars or their derivatives by glycosidation of the glycone is also disclosed.

REFERENCES:
patent: 4166848 (1979-09-01), Bernardi et al.
patent: 4181795 (1980-01-01), Whistler
patent: 4201773 (1980-05-01), Horton et al.
Stanek et al., "Monosaccharides", Academic Press, N.Y., NY 1963.
Pelyvas and Whistler, "Synthesis of L-Acosamine and 1-Thio-L-Acosamine Derivatives by the Stereoselective Reduction of O-Acetyloximes with Borane," Carbohydrate Research, 84 (1980) C5-C7.
Sztaricskai et al., "A Synthesis of 1-Ristosamine and a Derivative of Its C-4 Epimer," Carbohydrate Research, 65 (1978), 193-200.
Pelyvas et al., "A Convenient New Route to Methyl N,O-Diacetyl-.alpha.- L-Ristosaminide," Carbohydrate Research, 76 (1979), 257-260.

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