Method of preparing 23-monoesters of OMT and DMT

Details Method of preparing 23-monoesters of OMT and DMT Method of preparing 23-monoesters of OMT and DMT

1983-03-14

1984-12-11

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

536 185, 536115, 536119, C07H 100, C07H 1708

Patent

active

044879237

ABSTRACT:
An improved method of preparing 23-monoester derivatives of 5-O-mycaminosyl tylonolide (OMT) and demycinosyltylosin (DMT) is provided. This method comprises esterifying the antibiotic with an acylating agent in the presence of an external base, such as pyridine or 2,4,6-collidine, until acylation of the 23-hydroxyl group is substantially complete, and separating the 23-monoester derivative. 23-Monoester derivatives of OMT and DMT are useful antibiotics and/or intermediates to antibiotics.

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Derwent, Abstract, 83-729999/32, of German Patent 3301-959-A, Aug. 4, 1983, assigned to Toyo Jozo KK.
A. Tanaka et al., "Synthesis of Recyclized Macrolide Antibiotics and Related Derivatives from Mycaminosyl Tylonolide", Bull. Soc. Chem. Soc. Japan 54, 3837-3845, (1981).
A. Tanaka et al., "Synthesis of 4'-Deoxymycaminosyl Tylonolide", J. Antibiotics 34, 1374-1376, (1981).
A. Tanaka et al., "Syntheses of Derivatives of 4'-Deoxymycaminosyl Tylonolide and Mycaminosyl Tylonolide Modified at C-23", J. Antibiotics 34, 1377-1380, (1981).

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