6-methyl-(2,3,5-tri-O-benzyl-4-thio-α-L-lyxofuranosyl)cytosine | 675588-95-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 6-methyl-(2,3,5-tri-O-benzyl-4-thio-α-L-lyxofuranosyl)cytosine
• CAS: 675588-95-1
• 化学式: C₃₁H₃₃N₃O₄S
• 分子量: 543.687
• InChiKey: QYBAQEXRMKNEFU-ZJRZZCDQSA-N

反应信息

• 作为反应物：
  描述：

  6-methyl-(2,3,5-tri-O-benzyl-4-thio-α-L-lyxofuranosyl)cytosine 在 三溴化硼 、 silver carbonate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 1.5h， 以3%的产率得到6-methyl-1-(4-thio-α-L-lyxofuranosyl)cytosine
  参考文献：
  名称：

  Thiosugars. X. Novel Nucleoside Analogues Derived from 4-Thio-L-lyxofuranose

  摘要：

  1-O-Acetyl-2,3,5-tri-O-benzyl-4-thio-L-lyxofuranose 1 was transformed into O-benzyl- and O-acetyl-protected 1-(4-thio-L-lyxofuranosyl) nucleoside derivatives by use of the TMSOTf method. Debenzylation with boron tribromide or deacetylation with sodium methoxide yielded the corresponding pyrimidine (7-11, 17, 18, 26 and 27) and purine (29 and 34) nucleoside analogues. The anomeric configurations were determined by NMR spectroscopy and, in the case of the 5-halo- (7-9) and nitrouridine derivative 11 and the 6-methylcytidine derivative 27, by X-ray structural analyses. - The unprotected nucleosides were not antivirically inhibitory at 250 muM.

  DOI：

  10.1081/ncn-120025236
• 作为产物：
  描述：

  6-methyl-4-(1,2,4-triazol-1-yl)-1-(2,3,5-tri-O-benzyl-4-thio-α-L-lyxofuranosyl)-2(1H)-pyrimidinone 在 ammonium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以68%的产率得到6-methyl-(2,3,5-tri-O-benzyl-4-thio-α-L-lyxofuranosyl)cytosine
  参考文献：
  名称：

  Thiosugars. X. Novel Nucleoside Analogues Derived from 4-Thio-L-lyxofuranose

  摘要：

  1-O-Acetyl-2,3,5-tri-O-benzyl-4-thio-L-lyxofuranose 1 was transformed into O-benzyl- and O-acetyl-protected 1-(4-thio-L-lyxofuranosyl) nucleoside derivatives by use of the TMSOTf method. Debenzylation with boron tribromide or deacetylation with sodium methoxide yielded the corresponding pyrimidine (7-11, 17, 18, 26 and 27) and purine (29 and 34) nucleoside analogues. The anomeric configurations were determined by NMR spectroscopy and, in the case of the 5-halo- (7-9) and nitrouridine derivative 11 and the 6-methylcytidine derivative 27, by X-ray structural analyses. - The unprotected nucleosides were not antivirically inhibitory at 250 muM.

  DOI：

  10.1081/ncn-120025236