Hypophosphite deoxygenation reactions in the synthesis of erythr

Details Hypophosphite deoxygenation reactions in the synthesis of erythr Hypophosphite deoxygenation reactions in the synthesis of erythr

1998-03-06

2000-03-21

Crane, L. Eric

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

Organic compounds

Carbohydrates or derivatives

536 72, C07H 1708, C07H 103

Patent

active

06040440&

ABSTRACT:
A process for the preparation of 4"-deoxyerythromycins, having the formula: ##STR1## wherein R is H or OH, R.sup.1 is H or loweralkyl, and R.sup.2 is H or CH.sub.3 by treatment of the starting material, 2'-O-acetyl-4"-imidazolylthiocarbamoyl-erythromycin, with a hypophosphite reagent, in a water-miscible protic solvent optionally comprising a phase transfer agent. In a preferred embodiment, the water-miscible solvent is an alcohol and the starting material is reacted with sodium hypophosphite, ACVA and tetra-n-butylammonium hydroxide.

REFERENCES:
patent: 3478013 (1969-11-01), Jones et al.
patent: 5760198 (1998-06-01), Parekh et al.
Graham et al., "A New Initiator for Radical Deoxygenations: Application to the Synthesis of 4"-Deoxyerythromycins, " published Sep. 7-11, 1997, Las Vegas, NV, 214th American Chemical Society National Meeting, see entire document.
"Phase-Transfer Catalysis," in Eastman Organic Chemical Bulletin, 48(1), 1-2. 1976.
Gokel et al., "Phase Transfer Catalysis--Part I: General Principles," Journal of Chemical Education, 55(6), 350-354 (Jun., 1978).
Dehmlow, "Phasentransfer-Katalyse. Eine Veilseitige, Moderne Synthesetechnik mit Potentialler Bedeutung fur die Farbenchemie," Chimia, 34(1), 12-20 (Jan. 1980).
Graham et al., "A New Initiator for Radical Deoxygenations: Application to the Synthesis of 4"-Deoxyerythromycins," Abstract No. 22, ORGN, Abstract of Papers, Part 2, 214th National Meeting--American Chemical Society, Las Vegas, NV, Sep. 7-11, 1997.
Shankaran et al., "Preparation and Activities of 4"-Epi and 4"-Deoxy-4"-amino Analogs Derived from 9-Deoxo-8a-aza-8a-homoerythromycin A.sup.1," Bioorganic &Medicinal Chemistry Letters, 4(9), 1111-1116 (May 5, 1994).
Journal of Organic Chemistry, vol. 58, No. 24 , (1993), pp. 6838-6842, Barton et al., "The Invention of Radical Reactions. 32. Radical Deoxygenations, Dehalogenations, and Deaminations with Dialkyl Phosphites and Hypophosphorous Acid as Hydrogen Sources".
Heterocycles, vol. 42, No. 2 (1996), pp. 499-502, T. Sato et al., "Practical Radical Deoxygenation of Erythromycins by Barton Reaction".

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