A short route to 3′‐deoxy‐3′‐fluorothymidine

The 5-OH-protected methyl glycosides 2 and 3 were epimerized to give the corresponding epimers 6 and 7 via an oxidation-reduction procedure. Reaction of 6 with diethylamino-sulfur trifluoride (DAST) afforded the fluoro sugar 8, which was coupled with thymine to give 3′-deoxy-3′-fluorothymidine (12) after deprotection with saturated ammonia in methanol.

[1]  M. S. Motawia,et al.  A new route to 2′,3′‐dideoxycytidine , 1990 .

[2]  R. Pauwels,et al.  Anti-retrovirus activity of 3'-fluoro- and 3'-azido-substituted pyrimidine 2',3'-dideoxynucleoside analogues. , 1988, Biochemical pharmacology.

[3]  E. De Clercq,et al.  Potent and selective activity of 3'-azido-2,6-diaminopurine-2',3'-dideoxyriboside, 3'-fluoro-2,6-diaminopurine-2',3'-dideoxyriboside, and 3'-fluoro-2',3'-dideoxyguanosine against human immunodeficiency virus. , 1988, Molecular pharmacology.

[4]  E. De Clercq,et al.  3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents. , 1987, Journal of medicinal chemistry.

[5]  D W Barry,et al.  3'-Azido-3'-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro. , 1985, Proceedings of the National Academy of Sciences of the United States of America.

[6]  H. Vorbrüggen,et al.  Nucleoside syntheses, XXII1) Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts , 1981 .

[7]  B. Samuelsson,et al.  Oxidation of primary and secondary alcohols in partially protected sugars with the chromium trioxide-pyridine complex in the presence of acetic anhydride , 1978 .

[8]  W. Middleton New fluorinating reagents. Dialkylaminosulfur fluorides , 1975 .

[9]  G. Etzold,et al.  NUCLEOSIDE VON FLUORZUCKERN 6. MITT. SYNTH. UND REAKTIVITAET VON 3′-FLUOR- UND 3′-CHLOR-3′-DESOXY-THYMIDIN , 1971 .

[10]  E. Corey,et al.  New reagents for stereoselective carbonyl reduction. An improved synthetic route to the primary prostaglandins. , 1971, Journal of the American Chemical Society.

[11]  R. Pauwels,et al.  Anti-Hiv-1 Activity of 2′,3′-Dideoxinucleoside Analogues : Structure-Activity Relationship , 1989 .

[12]  M. Hirsch,et al.  Enhanced in vitro inhibition of HIV-1 replication by 3'-fluoro-3'-deoxythymidine compared to several other nucleoside analogs. , 1988, AIDS Research and Human Retroviruses.

[13]  A. Derome,et al.  Methyl 5-0--butyldiphenylsilyl-2-deoxy-α β -d--pentofuranoside as a divergent intermediate for the synthesis of 3'-substituted-2',3'-dideoxynucleosides: synthesis of 3'-azido-3'-deoxythymidine, 3'-deoxy-3'-fluorothymidine and 3'-cyano-3'-deoxythymidine. , 1988 .

[14]  F. Hansske,et al.  2' And 3'-ketonucleosides and their arabino and xylo reduction products: Convenient access via selective protection and oxidation of ribonucleosides☆ , 1984 .

[15]  N. Dyatkina,et al.  Aminonuclosides and Their Derivatives; XII1. A New Synthesis of 1-O-Methyl-3-azido-2,3-dideoxy-D-ribofuranose , 1984 .

[16]  D. Cech,et al.  NMR-spektroskopische Untersuchungen zum Konformations-verhalten von 2′- und 3′-halogensubstituierten Pyrimidinnucleosiden , 1983 .

[17]  G. Etzold,et al.  Nucleoside von Fluorzuckern. XII. Ein neuer Zugang zu 1-(2,3-Didesoxy-3-fluor-β-D-ribofuranosyl)-pyrimidinen , 1973 .

[18]  G. Etzold,et al.  Nucleoside von fluorzuckern- VI , 1971 .

[19]  B. R. Baker,et al.  Puromycin. Synthetic Studies. VIII. Synthesis of 3-Amino-3-deoxy-D-ribofuranoside Derivatives. A Second Synthesis of 3-Amino-3-deoxy-D-ribose , 1955 .