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

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

1990-04-27

1994-07-05

Siegel, Alan

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D33332

Patent

active

053268849

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:
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patent: 4739047 (1988-04-01), Volkmann et al.
patent: 4864046 (1989-09-01), Volkmann
patent: 4874877 (1989-10-01), Urban
patent: 4954647 (1990-09-01), Urban
Feiser and Fieser, Advanced Organic Chemistry, pp. 313, 319 (1961).
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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