Chiral synthesis of thienamycin from D-gluocose

Details Chiral synthesis of thienamycin from D-gluocose Chiral synthesis of thienamycin from D-gluocose

1983-02-07

1984-05-15

Raymond, Richard

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549 11, 549 22, 549 89, 549 90, 260349, 562426, 562556, C07D33324

Patent

active

044489765

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: 4324900 (1982-04-01), Durette

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