Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1992-03-31
1993-05-18
Rollins, John W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 283, 536 2852, 536 285, 536 2853, 536 2854, C07H 1700, C07H 1906
Patent
active
052122948
ABSTRACT:
There are disclosed novel processes for producing 2',3'-dideoxy-2'3'-didehydronucleosides, for example, 2',3'-dideoxy-2',3'-didehydrothymidine in high yields and on a large scale. The compounds so-produced are useful as antiviral agents, especially as agents effective against the human immunodeficiency viruses (HIV).
REFERENCES:
patent: 3322747 (1967-05-01), Shen et al.
Ruyle et al., "Nucleosides, II. Reactions of 5'-Trityluridine 2',3'-O-Thionocarbonate", J. Organic Chemistry, vol. 30(12), (1965), pp. 4353-4355.
Khwaja et al., "Fluorinated Pyrimidines. XXIX. syntheses of 2',3'-Dehydro-5-fluoro-2'-deoxyuridine and 2',3'-Dideoxy-5-fluorouridine.sup.1 ", Journal of Medicinal Chemistry, vol. 10 No. 6 (1967), pp. 1067-1069.
Barton et al., "Reactions of Relevance to the Chemistry of Aminoglycoside Antibiotics. Part 7. Conversion of Thiocarbonates into Deoxy-sugars", Journal of The Chemical Society, (1977), pp. 1718-1723.
Gibbs, "Facile high-yield synthesis of singly isomeric 2'3'-O-alkoxymethylidene adenosine", (1976), p. 4.
Adachi, "Synthetic Electrochemical Studies on Nucleosides. I. Novel Method for the Synthesis of 2',3',-Unsaturated Nucleosides via Electrolysis", J. Org. Chem., vol. 44, No. 9 (1979), pp. 1404-1409.
Robins et al., "A Mild conversion of Vicinal Diols to Alkenes. Efficient Transformation of Ribonucleosides into 2'-ENE and 2',3'-Dideoxynucleosides.sup.1 ", Tetrahedron Letters., vol. 25, No. 4, (1984) pp. 367-370.
Fuller Carl E.
Howell Henry G.
Mansuri Muzammil M.
Martin John C.
Starrett, Jr. John E.
Bristol--Myers Squibb Company
Nolan Sandra M.
Rollins John W.
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