Method of synthesis of azole-containing amino acids

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C548S339100, C548S232000, C548S229000, C546S121000

Reexamination Certificate

active

11170042

ABSTRACT:
The invention relates to methods of synthesizing 2-substituted azole compunds of formula (I):The invention is also relates to compounds of formula (I) and to intermediate compounds in the synthesis method.

REFERENCES:
Hecht et al. “Synthesis of L-erythro-beta-Hydroxyhistidine from D-Glucosamine”.J. American Chem. Soc., 1979, pp. 3982-3983 vol. 101. XP002371212.
Garner P. Stereocontrolled Addition To A Penaldic Acid Equivalent: An Asymmetric Synthesis of Threo-β-Hydroxy-L-Glutamic Acid. Tetrahedron Lett., 1984, pp. 5855-5858, vol. 25, No. 51.
Otsuka M. et al. “Synthetic study towards man-designed bleomycins. Synthesis of a DNA cleaving molecule based on bleomycin”Tetrahedron Letters. 1986, pp. 3639-3642, vol. 27, No. 31, XP002371210.
Kittaka A. et al. “Transition-metal binding site of bleomycin. A remarkably efficient dioxygen-activating molecule based on bleomycin-FE(II) complex”.Tetrahedron Letters, 1986, pp. 3631-3634, vol. 27, No. 31, XP002371211.
Kittaka et al. “Synthetic models for the transition metal binding site of bleomycin. Remarkable Improvement of dioxygen activating capability”.Tetrahedron, 1988, pp. 2811-2820, vol. 44, No. 10.
Lubell, W. et al., “Surrogates for Chiral Aminomalondialdehyde. Synthesis of N-(9-Phenylfluoren-9-yl) serinal and N-(9-Phenylfluoren-9-yl)vinylglycinal.”J. Org. Chem., 1989, pp. 2824-2831, vol. 54.
Dondoni A. et al., “Stereochemistry Associated with the Addition of 2-(Trimethylsilyl)thiazole to Differentially Protected α-Amino Aldehydes. Applications toward the Synthesis of Amino Sugars and Sphingosines.”J. Org. Chem. 1990, pp. 1439-1446, vol. 55.
Saeed, A., “Synthesis of L-β-Hydroxyaminoacids Using Serine Hydroxymethyltransferase.”Tetrahedron, 1992, pp. 2507-2514, vol. 48, No. 12.
Dondoni A. et al. “2-Thiazolyl-Amino Ketones: A new class of reactive intermediates for the stereocontrolled synthesis of unusual amino acids”.Synthesis, 1993, pp. 1162-1176, vol. 11, XP002371216.
Dondoni A. et al. “Chelation-and Non-chelation-controlled addition of 2-(Trimethylsilyl)thiazole to alpha-Amino Aldehydes: Stereoselective synthesis of the beta-amino-alpha-hydroxy Aldehyde.” Stereoselective Synthesis of the β-Amino-α-hydroxy Aldehyde Intermediate for the Preparation of the Human Immunodeficiency Virus Proteinase Inhibitor Ro 31-8959.J. Org. Chem., 1995, pp. 8074-8080, vol. 60, No. 24, XP002371214.
Dondoni A. et al: “Total synthesis of (+)-Galactostatin. An Illustration of the utility of the thiazole-aldehyde synthesis”.J. Org. Chem., 1995, pp. 4749-4754, vol. 60, No. 15, XP002371215.
Kimura T., “Enzymatic Synthesis of β-Hydroxy-α-amino Acids Based on Recombinant D- and L-Threonine Aldolases.”J. Am. Chem. Soc., 1997, pp. 11734-11742, vol. 119.
Zhao, M. et al., “Oxidation of Primary Alcohols to Carboxylic Acids with Sodium Chlorite Catalyzed by TEMPO and Bleach.”J. Org. Chem. 1999, pp. 2564-2566, vol. 64.
Liang, X. et al., “Garner's aldehyde”Royal. Soc. Chem., 2001, pp. 2136-2157.
Palian, M.M. et al., “Lipo α-Amino-β-hydroxy Acids and O-Linked Glycosides: Building Blocks for Ceramyl and Glycosphingoyl Peptides.”J. Org. Chem., 2001, pp. 7178-7183, vol. 66.
Dong et al. “Total Synthesis of Exochelin MN and Analogues”.J. Org. Chem., 2002, pp. 4759-4770, vol. 67, No. 14, XP002371209.
Barma, D.K. et al., “Dimethylthiocarbamate (DMTC): An Alcohol Protecting Group.9”Organic Letters, 2003, pp. 4755-4757, vol. 25, No. 25.
PCT International Search Report dated Mar. 21, 2006 for PCT Application No. PCT/US2005/023048 which relates to U.S. Appl. No. 10/170,042.

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

Method of synthesis of azole-containing amino acids does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method of synthesis of azole-containing amino acids, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of synthesis of azole-containing amino acids will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3851115

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