117174-38-6

Basic information

• Product Name: 1-(3-cyano-2,3-dideoxy-beta-D-threo-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione
• Synonyms: 1-(3-C-Cyano-2,3-dideoxy-beta-D-arabino-pentofuranosyl)thymine; 2,4(1H,3H)-Pyrimidinedione, 1-(3-cyano-2,3-dideoxy-.beta.-D-threo-pentofuranosyl)-5-methyl-; 2,4(1H,3H)-Pyrimidinedione, 1-(3-cyano-2,3-dideoxy-beta-D-threo-pentofuranosyl)-5-methyl-
• CAS NO: 117174-38-6
• Molecular Formula: C₁₁H₁₃N₃O₄
• Molecular Weight: 251.2386
• Mol File: 117174-38-6.mol
• Article Data: 4

Chemical Properties

• Density: 1.44g/cm³
• Refractive Index: 1.6
• CAS DataBase Reference: 1-(3-cyano-2,3-dideoxy-beta-D-threo-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-cyano-2,3-dideoxy-beta-D-threo-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione(117174-38-6)
• EPA Substance Registry System: 1-(3-cyano-2,3-dideoxy-beta-D-threo-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione(117174-38-6)

Safety Data

• Hazardous Substances Data: 117174-38-6(Hazardous Substances Data)

Upstream product

• 117174-37-5 1-<3'-C-cyano-2',3'-dideoxy-5'-O-(t-butyldimethylsilyl)-β-D-threo-pentofuranosyl> thymine 
• 121336-21-8 1-(3'-cyano-2',3'-dideoxy-5'-O-trityl-β-D-threo-pentofuranosyl)thymine 
• 115913-84-3 1-(2,3-epoxy-5-O-trityl-β-D-lyxo-pentofuranosyl)thymine 
• 115941-56-5 1-(3-cyano-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine 
• 121336-20-7 (2S,5R)-5-(5-Methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-2,5-dihydro-furan-3-carbonitrile 
• 117174-33-1 1-<2,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl>thymine 
• 117174-35-3 1-(3'-C-cyano-3'-deoxy-β-D-xylo-pentofuranosyl)thymine 
• 117174-36-4 1-(5'-O-(t-butyldimethylsilyl)-3'-C-cyano-3'-deoxy-β-D-xylo-pentofuranosyl)thymine 
• 117174-32-0 1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine 
• 117174-34-2 1-(2',5'-di-O-(t-butyldimethylsilyl)-3'-C-cyano-3'-deoxy-β-D-xylo-pentoifuranosyl)thymine 
• 117174-40-0 (2R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-carbonitrile 
• 118222-09-6 Thiocarbonic acid O-[(2R,3R,4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-cyano-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester O-phenyl ester 
• 118222-05-2 1-(2',5'-di-O-(t-butyldimethylsilyl)-3'-C-cyano-3'-O-(phenyloxythiocarbonyl)-β-D-pentofuranosyl)thymine 
• 1463-10-1 5-Methyluridine 

Relevant articles and documents

Synthesis of the Dideoxynucleosides ddC and CNT from Glutamic Acid, Ribonolactone, and Pyrimidine Bases

2,3-Dideoxyribose in suitably protected form was prepared from glutamic acid and coupled with silylated cytosine to give a mixture of the α-and β-anomers of 2',3'-dideoxycitidine.The anomer ratio depended on the Lewis acid used in the coupling, with EtAlCl2 favoring the β-anomer ddC, a potent anti-HIV drug.Conjugate addition of cyanide to a 4-butenolide prepared from D-ribonolactone gave a mixture of (racemic) α- and β-3-cyanobutyrolactones.Both isomers were reduced to lactols and coupled with thymine to give α/β-anomer pairs.The α-cyano lactone, the struct ure of which was established by X-ray crystallography, afforded an authentic sample of the putative (but in fact inactive) anti-HIV substance known in AIDS research as CNT.

3'-C-cyano-3'-deoxythymidine

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