Process for deoxygenating secondary alcohols

Details Process for deoxygenating secondary alcohols Process for deoxygenating secondary alcohols

1976-07-12

1978-03-07

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

2603972, 2603974, 2603975, 260429R, 2604297, 260452, 260455R, 260463, 260596, 260603R, 260638R, 260666R, 424180, 424181, 424182, 536 1, 536 4, 536 10, 536 26, 536115, 536121, 560106, 548341, C07H 1522, C07J 3100

Patent

active

040781399

ABSTRACT:
The process for removing a secondary hydroxyl group from an organic compound having at least one secondary hydroxyl group and having any amino groups protected, comprises the reaction of a reactive ester of said secondary hydroxyl group selected from the group consisting of an O-alkylthioester and an O-alkylselenoester with at least one mole of an organotin hydride, preferably tri-n-butylstannane, in an inert, aprotic solvent at a temperature of at least about 100.degree. C and under an inert atmosphere.
The process is particularly useful in removing secondary alcohols in aminoglycoside antibiotics to produce deoxy derivatives thereof having antibacterial activity.
Also described are novel O-sec.-alkylthiobenzoate, O-sec.-alkyl-S-methylxanthate, N-(sec.-alkoxythiocarbonyl)-imidazole esters, and di-O-alkylthiocarbonates having at least one secondary O-alkyl group, useful intermediates of the claimed process.

REFERENCES:
patent: 3828021 (1974-08-01), Beattie et al.
patent: 3868360 (1975-02-01), Daniels et al.
patent: 3920628 (1975-11-01), Daniels
Perkins, "J. Chem. Soc.," No. 16, pp. 1574-1585, 1975.
Hitoshi, et al., "Chem. Abst.," vol. 76, 1972, pp. 127, 293x.

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