4-amino-1-[(2R,3E,4S,5R)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Tezacitabine is a ribonucleotide reductase inhibitor. It is a synthetic purine nucleoside analogue with potential antineoplastic activity. It is used for DNA synthetic.[1]
EP 0372268; JP 1990178272; US 5378693 The acetylation of uridine (I) with acetic anhydride gives the 2′,3′,5′-triacetyl derivative (II), which is treated with SOCl2 and sodium ethoxide yielding the 4-ethoxypyrimidinone (III). The partial protection of (III) with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (IV) yields the silylated compound (V), which is oxidized with oxalyl chloride to the silylated furanone (VI). The reaction of (VI) with fluoromethyl phenyl sulfone (A) by means of diethyl chlorophosphate (B) and lithium hexamethyldisylazide in THF affords the fluorovinyl sulfone (VII) as a mixture of (E) and (Z) isomers that is separated by flash chromatography. The (Z)-isomer (VII) is treated with tributyl tin hydride and AIBN in refluxing benzene to give the fluorovinyl stannane (VIII), which is finally treated with CsF and NH3 in refluxing methanol to afford the target compound. 
US 5607925
http://www.drugfuture.com/synth/syndata.aspx?ID=165222
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http://www.google.com/patents/WO2005049563A2?cl=en 
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5-30-2012
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HIGH MOLECULAR WEIGHT DERIVATIVE OF NUCLEIC ACID ANTIMETABOLITE
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9-12-2003
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Stable compositions comprising tezacitabine
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References
- Tsimberidou AM, Alvarado Y, Giles FJ (August 2002). “Evolving role of ribonucleoside reductase inhibitors in hematologic malignancies”. Expert Rev Anticancer Ther 2 (4): 437–48. doi:10.1586/14737140.2.4.437. PMID 12647987.
Filed under: Uncategorized Tagged: Tezacitabine
