Total synthesis of chiral 2-amino-1,3-diols

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

548243, 552 10, 564487, 564507, 564360, C07C20942

Patent

active

050120000

ABSTRACT:
A method for the preparation of chiral 2-amino-1,3-diols is disclosed. The method involves four steps including performance of an aldol condensation with a chiral oxazolidinone on an aldehyde, treating the aldol condensation product with an alkali metal azide, treating the product with a borohydride reagent and reducing the azide to an amine.

REFERENCES:
D. A. Evans, J. V. Nelson and T. R. Taber; Top. Stereochem., 13, 1(1982).
"A Practical and Enantioselective Synthesis of Glycoshingolipids and Related Compounds. Total Synthesis of Globotriaosylceramide (Gb.sub.3)" by K. C. Nicolaou et al.
"The Total Synthesis Sphingosine", J. Am. Chem. Soc., vol. 80, pp. 1194, 2170, (1958).
"A Steroselective Synthesis of Sphingosine, A Protein Kinase C Inhibitor", Tetrahedron Letters, vol. 29, No. 25, pp. 3037-3040, (1988).
"Synthesis of D-Eyrthrosphingosines", Tetrahedron Letters, vol. 27, p. 481, (1986).
"Synthesis of D-Erythro-1-Deoxydihydroceramide-1-Sulfonic Acid", Tetrahedron Letters, vol. 29, p. 1185, (1988).
M. Schlosser and K. F. Christmann, Ann Fur Chemie, vol. 708, p. 1, et seq., (1967).
"Synthesis of Erythrosphingosines Via Their Azido Derivatives", Liebigs Ann. Ch., pp. 663-667, (1988).
"Asymmetric Synthesis of Anti-B-Hydroxy-alpha-Amino Acids", Tetrahedron Letters, vol. 28, pp. 39-42, (1987).
"Asymmetric Glycine Enolate Aldol Reactions: Synthesis of Cyclosporine's Unusual Amino Acids", J. Am. Chem. Soc., vol. 18, pp. 6757-6761, (1986).
"Metal-Assisted Aldol Condensation of Chiral alpha-Halogenated Chiral Epoxide Synthesis", J. Am. Chem. Soc., vol. 108, pp. 4595-4602, (1986).
"Propane-1,3-dithiol: A Selective Reagent for the Efficient Reduction of Alkyl and Aryl Azides to Amines", Tetrahedron Letters, No. 39, pp. 3633-3634, (1978).
"Sodium Borohydride Reactions under Phase-Transfer Conditions: Reduction of Azides to Amines", J. Org. Chem., 47, 4327, (1982).
Y. Ito, M. Sawayara and T. Hayashi, Tetrahedron Letters, 29, 239, (1988).
D. A. Evans, J. V. Nelson, and T. R. Taber, Top. Sterochem., 13, 1(1982).
"A Practical and Enantioselective Synthesis of Glycoshingolipids and Related Compounds. Total Synthesis of Globotriaosylceramide (Gb.sub.3)", by K. C. Nicolaou et al.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Total synthesis of chiral 2-amino-1,3-diols does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Total synthesis of chiral 2-amino-1,3-diols, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Total synthesis of chiral 2-amino-1,3-diols will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-641705

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.