1-{5-O-t-butyldiphenylsilyl-2,3-di-O-[methylthio(thiocarbonyl)]-α-L-lyxofuranosyl}-5-fluorocytosine | 1382683-47-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-{5-O-t-butyldiphenylsilyl-2,3-di-O-[methylthio(thiocarbonyl)]-α-L-lyxofuranosyl}-5-fluorocytosine
• 英文别名: O-[(2S,3R,4R,5R)-5-(4-amino-5-fluoro-2-oxopyrimidin-1-yl)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-methylsulfanylcarbothioyloxyoxolan-3-yl] methylsulfanylmethanethioate
• CAS: 1382683-47-7
• 化学式: C₂₉H₃₄FN₃O₅S₄Si
• 分子量: 679.954
• InChiKey: GNXYQYIPDNRZBU-XJTUCQONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  210
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-{5-O-t-butyldiphenylsilyl-2,3-di-O-[methylthio(thiocarbonyl)]-α-L-lyxofuranosyl}-5-fluorocytosine 在 偶氮二异丁腈 、 dibutyl(pentyl)stannane 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以76%的产率得到2',3'-dideoxy-5-fluoro-5'-O-(tbutyldiphenylsilyl)-α-L-cytidine
  参考文献：
  名称：

  Total Synthesis of α-Elvucitabine

  摘要：

  Total synthesis of alpha-elvucitabine was achieved in 26% overall yield by a concise nine-step procedure starting from L-lyxose, with trimethylsilyl trifluoromethaneoulfonate (TMSOTf)-mediated stereocontrolled alpha-N-glycosidation and olefination through Barton-McCombie deoxygenation being the key steps, and the stereochemistry of the product was determined by nuclear Overhauser effect spectroscopy.

  DOI：

  10.1080/00397911.2011.571805
• 作为产物：
  描述：

  methyl L-lyxofuranoside 在 吡啶 、 咪唑 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 氨 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 1-{5-O-t-butyldiphenylsilyl-2,3-di-O-[methylthio(thiocarbonyl)]-α-L-lyxofuranosyl}-5-fluorocytosine
  参考文献：
  名称：

  Total Synthesis of α-Elvucitabine

  摘要：

  Total synthesis of alpha-elvucitabine was achieved in 26% overall yield by a concise nine-step procedure starting from L-lyxose, with trimethylsilyl trifluoromethaneoulfonate (TMSOTf)-mediated stereocontrolled alpha-N-glycosidation and olefination through Barton-McCombie deoxygenation being the key steps, and the stereochemistry of the product was determined by nuclear Overhauser effect spectroscopy.

  DOI：

  10.1080/00397911.2011.571805

文献信息

• Total Synthesis of α-Elvucitabine
  作者：Guilong Zhao、Yuanyuan Lou、Linshan Zhang、Hua Shao、Weiren Xu、Lida Tang、Meixiang Zou

  DOI：10.1080/00397911.2011.571805

  日期：2012.10

  Total synthesis of alpha-elvucitabine was achieved in 26% overall yield by a concise nine-step procedure starting from L-lyxose, with trimethylsilyl trifluoromethaneoulfonate (TMSOTf)-mediated stereocontrolled alpha-N-glycosidation and olefination through Barton-McCombie deoxygenation being the key steps, and the stereochemistry of the product was determined by nuclear Overhauser effect spectroscopy.