Processes for the diastereoselective separation of nucleoside an

Details Processes for the diastereoselective separation of nucleoside an Processes for the diastereoselective separation of nucleoside an

1995-06-05

1997-09-02

Kight, John

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

Organic compounds

Carbohydrates or derivatives

549 63, 549 62, 549430, 536 41, C07H 1900, C07D33332, C07D33334

Patent

active

056633203

ABSTRACT:
The present invention relates to highly diastereoselective processes for production of cis-nucleosides and nucleoside analogues and derivatives in high optical purity and intermediates useful in those processes.

REFERENCES:
patent: 4231945 (1980-11-01), McCombie
patent: 4383114 (1983-05-01), Vince
patent: 5204466 (1993-04-01), Liotta et al.
patent: 5210085 (1993-05-01), Liotta et al.
Goodman, "Chemical Syntheses and Transformations of Nucleosides," in Basic Principles in Nucleic Ac id Chemistry, vol. 1, Academic Press, New York, 1974, pp. 106-110.
March, Advanced Organic Chemistry, McGraw-Hill Book Co., New York, 1968, pp. 896-897.
M. Fieser, Reagents for Organic Synthesis, vol. 8, Wiley-Interscience, New York, 1980, pp. 261-263.
M. Fieser, Reagents for Organic Synthesis, vol. 12, Wiley-Interscience, New York, 1986, pp. 543-547.
Chu et al., "Synthesis and Structure-Activity Relationships of 6-Substituted 2',3'-Dideoxypurine Nucleosides as Potential Anti-Human Immunodeficiency Virus Agents," J. Med. Chem., 33(6), 1553-1561 (1990).
Farina et al., "a New Synthesis of 2',3'-Dideoxynucleosides for AIDS Chemotherapy," Tett. Letters, 29(11), 1239-1242 (1988).
Mansuri et al., "Preparation of the Geometric Isomers of DDC, DDA, D4C and D4T as Potential Anti-HIV Agents," Bioorganic & Medicinal Chem. Letters, 1(1), 65-68 (1991).
Vince et al., "Synthesis of Anti-HIV Activity of Carbocyclic 2',3'-Didehydro-2',3'-dideoxy-2,6-Disubstituted Purine Nucleosides," J. Medicinal Chem., 33(1), 17-21 (1990).
Wilson et al., "The Synthesis and Anti-HIV Activity of Pyrimidinyl Dioxolanyl Nucleosides", Bioorganic & Medicinal Chem. Letters, 3(2), 169-174 (1993).
J.W. Beach et al., "Synthesis of Enantiomerically Pure (2',R,5+s)-(-)-1-[2-(hydroxymethyl)oxathiolan-5-yl]cytosine as a Potent Antiviral Agent Against Hepatitis B Virus (HBV) and Human Immunodeficiency Virus (HIV)", J. Org. Chem., vol. 57, pp. 2217-2219 (1992).
B.R. Belleau, et al., "Oxidative Degradation of L-Ascorbic Acid Acetals to 2',3'-Dideoxy-3'-Oxaribofuranosides. Synthesis of Enantiomerically Pure 2',3'-Dideoxy-3'-Oxacytidine Stereoisomers as Potential Antiviral Agents", Tetrahedron Lett., vol. 33, pp. 6949-6952 (1992).
W-B. Choi, et al., "In Situ Complexation Directs the Stereochemistry of N-Glycoslylation in the Synthesis of Oxathiolanyl and Dioxolanyl Nucleoside Analogues", J. Am. Chem. Soc., vol. 113, pp. 9377-9379 (1991).
W-B. Choi, et al., "Synthesis, Anti-Human Immunodeficiency Virus, and Anti-Hepatitis B Virus Activity of Pyrimidine Oxathiolane Nucleosides", Bioorg. & Med. Chem. Lett., vol. 3(4), pp. 693-696 (1993).
C.K. Chu et al., "Enantiomeric Synthesis of (+)-BCH-189 [(+)-(2S,5R)-1-[2-(Hydroxymethyl)-1'',3-oxathiolan-5-yl]cytosine] from D-Mannose and Its Anti-HIV Activity", J. Org. Chem., vol. 56, pp. 6503-6505 (1991).
P. Faury, et al., "Synthesis of Tetrazole Oxathiolane Nucleoside Analogues and Their Evaluation of HIV-1 Antiviral Agents", Nucleosides & Nucleotides, vol. 11(8), pp. 1481-1488 (1992).
G. Hesse et al., "Mercapto-acetaldehyd und Dioxy-1,4-dithian", Chem. Ber., vol. 85, pp. 924-932 (1952).
D.C. Humber et al., "Expeditious Preparation of (-)-2'-Deoxy-3'-Thiacytidine (3TC)", Tetrahedron Lett., vol. 33, pp. 4625-4628 (1992).
L.S. Jeong, et al., "An Efficient Synthesis of Enantiomerically Pure (+)-(2S,5R)-1-[2-(Hydroxymethyl)-1,3-Oxathiolan-5-yl)cytosine (+)-BCH-189] from D-Galactose", Tetrahedron Lett., vol. 33, pp. 595-598 (1992).
L.S. Jeong, et al., "Asymmetric Synthesis and Biological Evaluation of .beta.-L-(2R,5S)-and .alpha.-L-(2R,5R)-1,3-Oxathiolane-Pyrimidine and -Purine Nucleosides as Potential Anti-HIV Agents", J. Med. Chem., vol. 36, pp. 181-195 (1993).
L.S. Jeong, et al., "Structure-Activity Relationships of .beta.-D-(2S,5R)-and .alpha.-D-(2S,5S)-1,3-Oxoathiolanyl Nucleosides as Potential Anti-HIV Agents", J. Med. Chem., vol. 36, pp. 2627-2638 (1993).
H. Jin, et al., "Unexpected Effects of Lewis Acids in the Synthesis of Optically Pure 2'-Deoxy-3'-Oxayctidine Nucleoside Analogues", Tetrahedron: Asymmetry, vol. 4(2), pp. 211-214 (1993).
J.L. Kraus, et al., "Synthesis of New 2,5-Disubstituted 1,3-Oxathiolanes. Intermediates in Nucleoside Chemistry", Synthesis, pp. 1046-1048 (1991).
J.M. McIntosh et al., "2-Mercaptoaldehyde Dimers and 2,5-Dihydrothiophenes From 1,3-Oxathiolan-5-ones", Can J. Chem., vol. 61, pp. 1872-1875 (1983).
R. Storer et al., "The Resolution and Absolute Stereochemistry of the Enantiomers of cis-1-[2-(Hydroxymethyl)-1,3-Oxathiolan-5-yl]Cytosine (BCH-189) : Equipotent Anti-HIV Agents", Nucleosides & Nucleotides, vol. 12, pp. 225-236 (1993).
E. Vedejs, et al., "Method for Sulfide S-Benzylation or S-Allylation Using Trimethylsilyl Triflate Activated Benzyl or Allyl Ethers", J. Org. Chem., vol. 46, pp. 3353-3354 (1981).

Affiliated with

Also associated with

Rating

Processes for the diastereoselective separation of nucleoside an does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Processes for the diastereoselective separation of nucleoside an, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Processes for the diastereoselective separation of nucleoside an will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-309539