Enantiospecific synthesis of S-(+)-5,6-dihydro-4-(R-amino)-4H-th

Details Enantiospecific synthesis of S-(+)-5,6-dihydro-4-(R-amino)-4H-th Enantiospecific synthesis of S-(+)-5,6-dihydro-4-(R-amino)-4H-th

1990-04-18

1992-10-20

Ivy, C. Warren

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D49504

Patent

active

051571293

ABSTRACT:
5,6-Dihydro-4-(R-amino)-4H-thieno[2,3-b]-thiopyran-2-sulfonamide-7,7-dioxid e is a potent carbonic anhydrase inhibitor useful in the treatment of ocular hypertension and glaucoma. The S-(+)-enantiomer of that compound, the more active enantiomer, is prepared by a process involving an intermediate step of an enantioselective reduction of a carbonyl group employing an oxazaborolidine chiral catalyst.

REFERENCES:
patent: 4677115 (1987-06-01), Baldwin et al.
patent: 4797413 (1989-01-01), Baldwin et al.
patent: 4946859 (1990-08-01), Hoffman, Jr. et al.
Morrison & Boyd, 3rd Ed. "Organic Chemistry", p. 630, Reduction to Alcohols.
Morrison & Boyd, 3rd Ed. "Organic Chemistry", p. 737, Conversion of RCH.sub.2 OH into RCH.sub.2 NH.sub.2.
Merck Index, 10th Ed. p. ONR-96, "Williamson Synthesis".
Corey et al., J. Amer Chem Soc., 1987, 109, 7925-7926.
Corey et al., J. Amer Chem Soc., 1987, 109, 5551-5553.
Corey et al., J. Org Chem., 1988, 53, 2861-2863.
Corey et al., Tet. Letters, 1989, 30, 5547-5550.
Corey et al., Tet. Letters, 1989, 30, 6275-6278.
Corey et al., Tet. Letters, 1990, 31, 611-614.
Youn et al., Tet. Letters, 1988, 29, 4453-4456.
Itsuno et al., J. Chem Soc., Perk. Trans. 1984, 1, 2887.
Itsuno et al., J. Chem Soc., Chem. Commun. 1983, 469.
Corey et al., Tet. Letters, 1990, 31, 601-604.
Itsuno et al., J. Org Chem., 1984, 49, 555-557.
Itsuno et al., Bull Chem Soc Japan, 1987, 60, 395-397.

Affiliated with

Also associated with

Rating

Enantiospecific synthesis of S-(+)-5,6-dihydro-4-(R-amino)-4H-th does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Enantiospecific synthesis of S-(+)-5,6-dihydro-4-(R-amino)-4H-th, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Enantiospecific synthesis of S-(+)-5,6-dihydro-4-(R-amino)-4H-th will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-193079