Synthesis of thienamycin from D-glucose

Details Synthesis of thienamycin from D-glucose Synthesis of thienamycin from D-glucose

1981-03-30

1983-05-24

Berch, Mark L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602452T, 260349, 2603303, 549 22, 536 41, 536122, 560153, C07D20508, C07D48704

Patent

active

043849989

ABSTRACT:
Disclosed is a chiral, total synthesis of thienamycin from D-glucose which proceeds via intermediates I, II and III to known aldehyde IV which is known to be useful in the total synthesis of thienamycin (V): ##STR1## wherein: R is lower alkyl having 1-6 carbon atoms or bi-valent alkyl having 2-6 carbon atoms which joins the two sulfur atoms; R.sup.1 is lower alkyl or aralkyl, such as benzyl and the like; and R.sup.2 is hydrogen or a removable protecting group, such as triorganosilyl wherein the organo groups are independently selected from lower alkyl, phenyl and phenylloweralkyl.

REFERENCES:
patent: 4234596 (1980-06-01), Christensen et al.
S. Hanessian and R. Fords, Abst. Papers, 181st ACS National Meeting, CARB 27(1981).

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