Process for optically active 3-(methane-sulfonyloxy) thiolane an

Details Process for optically active 3-(methane-sulfonyloxy) thiolane an Process for optically active 3-(methane-sulfonyloxy) thiolane an

1989-07-19

1990-09-04

Siegel, Alan

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

Organic compounds

Sulfonate esters

549 66, C07C14102

Patent

active

049546473

ABSTRACT:
Intermediates and a stepwise process for the conversion of D-methionine or certain of its derivatives to optically active compounds of the formula ##STR1## wherein R is (C.sub.1 -C.sub.3)alkyl, phenyl or tolyl. The latter compounds are in turn useful as an intermediate in the preparation of penem antibiotic 5R,6S-6-(1R-hydroxyethyl)-2-(1R-oxo-3S-thiolanylthio)-2-penem-3-carboxylic acid and corresponding pharmaceutically acceptable salts and esters.

REFERENCES:
patent: 4619924 (1986-10-01), Hamanaka
patent: 4739047 (1988-04-01), Volkmann et al.
patent: 4864046 (1989-09-01), Volkmann
Kleeman et al., Angew. Chemie Int. Ed. Engl., 18, 797 (1979).
Steadman et al., J. Agric. Food Chem., 23, 1137-1143 (1975).

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