Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1990-11-14
1993-07-13
Brown, Johnnie R.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 174, 536 179, 536 553, 536 54, 546219, 502339, C07H 100, B01J 2342, B01J 2100, C07D21140
Patent
active
052274799
ABSTRACT:
The present invention relates to an efficient new route for the preparation of (+)-nojirimycin and (+)-1-deoxynojirimycin which involves the stereoselective reductive amination of 1,2-O-isopropylidene-5-oxo-.alpha.-D-glucuronolactone. The reductive amination uses particular oximes of the 5-oxo compound.
REFERENCES:
patent: 4634765 (1987-01-01), Liu
patent: 4908439 (1990-03-01), Anzeveno
Mattingly et al., J. Org. Chem. 1983, 48, 3556 3559.
Lindsay, et al., Phenyl Azide (Benzene, azido-), Organic Syntheses Collective Volume 3, pp. 710-711, 1955.
Tsuda et al., Chemical and Pharmaceutical Bulletin, vol. 37, No. 10, pp. 2673-2678, (1989).
Stasik et al., C.R. Acad. Sci., Ser. 2, 1990, 311(5), 521.
Inouye et al., Tetrahedron, 24, 2125 (1968).
Saeki et al., Chem. Pharm. Bull., 16, 2477 (1968).
Kinast et al., Angew. Chem. Int. Ed. Engl., 20, 805 (1981).
Bernotas et al., Tetrahedron Letters, 26, 1123 (1985).
Bashyal et al., Tetrahedron, 43, 415 (1987).
Tsuda et al., Heterocycles, 27, 63 (1988).
Rajanikanth et al., Tetrahedron Letters, 30, 755 (1989).
Fleet et al., Tetrahedron Letters, 31, 405 (1990).
Fleet et al., Tetrahedron Letters, 31, 409 (1990).
Anzeveno et al., Tetrahedron Letters, 31, 2085 (1990).
Reitz et al., Tetrahedron Letters, 31, 6777 (1990).
Morrison and Boyd, "Organic Chemistry" 3rd Edition, published 1982 by Allyn and Bacon, Inc. (Boston), see p. 640.
Anzeveno Peter B.
Creemer Laura J.
Brown Johnnie R.
Kolano John J.
Merrell Dow Pharmaceuticals Inc.
White Everett
LandOfFree
Process for the preparation of nojirimycin and related compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for the preparation of nojirimycin and related compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of nojirimycin and related compounds will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2313070