Process for the preparation of 2,2'-anhydro- and 2'-keto-1-(3',5

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

56 271, 56 285, 56 2851, 56 2852, 56124, C07H 1909

Patent

active

058080473

ABSTRACT:
A process for the preparation of compounds of the formula: ##STR1## wherein Pg and R are protecting groups and B is a nucleobase. The process uses protected nucleobases to form 2,2'-anhydro nucleosides having the formula ##STR2## which are hydrolyzed to 2'-hydroxy intermediates which are then oxidized to the desired 2'-keto compounds. The compounds and intermediates are useful as antiviral and antitumor agents and as intermediates to 2,2'-anhydro-1-(.beta.-D-arabinofuranosyl)cytosine (anhydro-ara-C) and 1-.beta.-D-arabinofuranosylcytosine (Ara-C).

REFERENCES:
patent: 4526988 (1985-07-01), Hertel
patent: 4652554 (1987-03-01), Chwang
patent: 4808614 (1989-02-01), Hertel
patent: 4965374 (1990-10-01), Chou et al.
patent: 5047520 (1991-09-01), Matsuda et al.
patent: 5223608 (1993-06-01), Chou et al.
Kochetkov et al., Organic Chemistry of Nucleic Acids, Part B, Plenum Press, New York, NY, 1972, pp. 465-466, see citation 166.
Goodman, "Chemical Syntheses and Transformations of Nucleosides," Ch. 2 in Basic Principles in Nucleic Acid Chemistry, Academic Press, New York, NY, 1974, pp. 142-143 (see citations 206-206e) pp. 177-190 (see relevant citations).
Rosenthal et al., "Nucleosides of Branched-Chain Nitromethyl, Cyanomethyl, and Aminomethyl Sugars," Tetrahedron Letters, (48), 4233-4235 (1970).
Cook & Moffatt, "Carbodiimide-Sulfoxide Reactions. VI. Syntheses of 2'-and 3'-Ketouridines," J. Am. Chem. Soc., 89(11), 2697-2705 (1967).
Brodbeck & Moffatt, "Carbodiimide-Sulfoxide Reactions. IX. Synthesis of 2'-and 3'-Keto Derivatives of Cytidine," J. Organic Chemistry, 35(10), 3552-3558 (1970).
Tarkoy et al., "Nucleic-Acid Analogues with Constraint Conformation Flexibility in the Sugar-Phosphate Backbone (`Bicyclo-DNA`)," Helvetica Chimica Acta, 76, 481-510 (1993).
Robins et al.(I), "Periodinane Oxidation, Selective Primary Deprotection, and Remarkably Stereoselective Reduction of tert-Butyldimethylsilyl-Protected Ribonucleosides. Synthesis of 9-(.beta.-D-Xylofuranosyl)adenine or 3'-Deuterioadenosine from Adenosine," J. Organic Chemistry, 55(2), 410-412 (1990).
Chladek et al., "Aminoacyl Derivatives of Nucleosides, Nucleotides, and Polynucleotides. XVIII. Synthesis of 2'(3')-O-Aminoacyl Derivatives of Dinucleoside Phosphates," J. Organic Chemistry, 39(15), 2187-2193 (1974).
Kondo et al.(I), "Studies on Biologically Active Nucleosides and Nucleotides. 7. Synthesis of some N.sup.4 -Acylaminomethyl 2,2'-Anhydronucleosides," J. Organic Chemistry, 45(9), 1577-1581 (1980).
Kanai et al., "Pyrimidine Nucleosides. III. Reaction of Cytidine or N.sup.4 -Acetylcytidine with Partially Hydrolyzed Phosphorus Oxychloride," Chem. Pharm. Bull., 18(12), 2569-2571 (1970).
Furukawa et al., "A Direct Synthesis of 3', 5'-Di-O-Acetyl-)2,2'-cyclouridine," Chem. Pharm. Bull., 16(11), 2286-2288 (1968).
Kondo et al.(II), "Studies on Biologically Active Nucleosides and Nucleotides. @. A Convneint One-Step Synthesis of 2,2'-Anhydro-1-(3',5'-di-O-acyl-.beta.-D-arabinofuransyl)pyrimidines From Pyrimidine Ribonucleosides," J. Organic Chemistry, 42(17), 2809-2812 (1977).
Brodbeck et al., "Carbodiimide-Sulfoxide Reactions. IX. Synthesis of 2'-and 3'-Keto Derivatives of Cytidine," J. Organic Chemistry, 35(10), 3552-3558 (1970).
Marcuccio et al., "Modified Nucleosides. II. Economical Synthesis of 2',3'-Dideoxycytidine," Nucleosides & Nucleotides, 11(10), 1695-1701 (1992).
Chwang et al. (III), "2'-O-Nitro-1-.beta.-D-arabinofuranosylcytosine. A New Derivative of 1-.beta.-D-arabinofuranosylcytosine That Resists Enzymatic Deamination and Has Antileukemic Activity," J. Medicinal Chemistry, 26(2), 280-288 (1983).
Samano et al., "Mild Periodinane Oxidation of Protected Nucleosides To Give 2'-and 3'-Ketonucleosides. The First Isolation of a Purine 2'-Deoxy-3'-ketonucleoside Derivative," J. Organic Chemistry, 55(18), 5186-5188 (1990).
Hansske et al.(I), "Nucleic Acid Related Compounds. 43. A Convenient Procedure for the Synthesis of 2' and 3'-Ketonucleosides," Tetrahedron Letters, 24(15), 1589-1592 (1983).
Hansske et al.(II), "2' and 3'-Ketonucleosides and Their Arabino and Xylo Reduction Products," Tetrahedron, 40(1), 125-135 (1994).
Robins et al. (II), "Nuclei Acid Rlated COmpounds. 74. Synthesis and Biological Activity of 2'(and 3')-Deoxy-2'(and 3')-methylenenucleoside Analogues That Function as Mechanism-Based Inhibitors of S-Adenosyl-L-homocysteine Hydrolase and/or Ribonucleotide Reductase," J. Medicinal Chemistry, 35(12), 2283-2293 (1992).
Ishida et al., "N.sup.4 -Acylnucleosides," Chem. Abstracts, 85, pp. 678-679, Abstr. N O. 124309g (1976); English language abstract of Japanese patent reference O supra attached to a complete copy of the patent in japanese.
Sakata et al., "Preparation of 1-(.beta.-D-Erythropentofuran-ulosyl)pyrimidines as Interemdiates for 188035e (1995); English language abstract of Japanese patent reference P supra attached to a complete copy of the patent in Japanese.

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

Process for the preparation of 2,2'-anhydro- and 2'-keto-1-(3',5 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 2,2'-anhydro- and 2'-keto-1-(3',5, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of 2,2'-anhydro- and 2'-keto-1-(3',5 will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-89136

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