118222-08-5

Basic information

• Product Name: (2S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-3-carbonitrile
• Synonyms: 3-Furancarbonitrile, 5-(3,4-dihydro-5-methyl-2,4-dioxo-1(2H)-pyrimidinyl)-2,5-dihydro-2-(hydroxymethyl)-, (2S,5R)-
• CAS NO: 118222-08-5
• Molecular Formula: C₁₁H₁₁N₃O₄
• Molecular Weight: 249.2227
• Mol File: 118222-08-5.mol
• Article Data: 4

Chemical Properties

• Density: 1.49g/cm³
• Refractive Index: 1.629
• CAS DataBase Reference: (2S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-3-carbonitrile(118222-08-5)
• EPA Substance Registry System: (2S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-3-carbonitrile(118222-08-5)

Safety Data

• Hazardous Substances Data: 118222-08-5(Hazardous Substances Data)

Upstream product

• 115941-56-5 1-(3-cyano-3-deoxy-5-O-trityl-β-D-arabinofuranosyl)thymine 
• 42926-80-7 5'-O-(4-monomethoxytrityl)-2'-deoxythymidine 
• 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 
• 118222-05-2 1-(2',5'-di-O-(t-butyldimethylsilyl)-3'-C-cyano-3'-O-(phenyloxythiocarbonyl)-β-D-pentofuranosyl)thymine 
• 1463-10-1 5-Methyluridine 
• 117174-34-2 1-(2',5'-di-O-(t-butyldimethylsilyl)-3'-C-cyano-3'-deoxy-β-D-xylo-pentoifuranosyl)thymine 
• 117174-32-0 1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine 
• 117174-36-4 1-(5'-O-(t-butyldimethylsilyl)-3'-C-cyano-3'-deoxy-β-D-xylo-pentofuranosyl)thymine 
• 117174-35-3 1-(3'-C-cyano-3'-deoxy-β-D-xylo-pentofuranosyl)thymine 
• 117174-33-1 1-<2,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl>thymine 
• 121417-05-8 1-<5'-O-(4-monomethoxytrityl)-β-D-glycero-pentofuran-3'-ulosyl>thymine 
• 158774-88-0 1-<5-O-(4-monomethoxytrityl)-3-deoxy-3-C-nitromethyl-β-D-xylo-pentofuranosyl>thymine 
• 115913-84-3 1-(2,3-epoxy-5-O-trityl-β-D-lyxo-pentofuranosyl)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 

Relevant articles and documents

New synthesis of 3′-c-substituted-3′-nitromethyl-ribo-thymidines

The 3′-exo-nitromethylene function in ribo-thymidine, as in 3, has been used for the first time as a general intermediate in the Michael addition reaction to give varieties of 3′-C-substituted nucleosides (12 - 21). The reaction of the conjugate base of acetylacetone with 3 however gave cis-fused furanose[3.2.1]hexopyranose nucleoside 24 as a major product due to the base catalyzed rearrangement of the initially formed Michael adduct 17. Detailed NMR spectroscopic data have been presented in support of the structural integrity of all reaction products.

Synthesis of 3'-C-cyano-3'-deoxy-pentofuranosylthymine nucleosides

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