tert-butyl-[[(2S,4S,5R)-5-(6-chloropurin-9-yl)-4-fluorooxolan-2-yl]methoxy]-diphenylsilane | 136228-17-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: tert-butyl-[[(2S,4S,5R)-5-(6-chloropurin-9-yl)-4-fluorooxolan-2-yl]methoxy]-diphenylsilane
• CAS: 136228-17-6
• 化学式: C₂₆H₂₈ClFN₄O₂Si
• 分子量: 511.071
• InChiKey: KSQPLHJRXBKRQE-CTIGNXTNSA-N

物化性质

• 沸点：
  591.3±60.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  62.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-chloro-9-trimethylsilylpurine 、 tert-butyl-[[(2S,4S,5R)-5-(6-chloropurin-9-yl)-4-fluorooxolan-2-yl]methoxy]-diphenylsilane 在 四丁基氟化铵 作用下， 以 乙酸乙酯 、 四氢呋喃 为溶剂， 生成 6-chloro-9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)-9H-purine 、 [(2S,4S,5S)-5-(6-chloropurin-9-yl)-4-fluorooxolan-2-yl]methanol
  参考文献：
  名称：

  A concise synthesis of anti-viral agent F-ddA, starting from (S)-dihydro-5-(hydroxymethyl)-2(3H)-furanone

  摘要：

  Anti-HIV agent beta-F-ddA (1) has been synthesized starting from readily available non-sugar, (S)-(+)-Dihydro-5-(hydroxymethyl)-2-(3H)-furanone (4). A highly sa n-stereoselective fluorination of the hydroxy lactone 2 generates the key intermediate fluorolactone 5 in a short and concise synthetic sequence. Reduction of 5 followed by bromination generates the aglycon which is glycosylated to generate F-ddA by amination and deprotection. Steric bulk of the 5-protecting group has minimal effect on the steric course of glycosylation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02532-7
• 作为产物：
  描述：

  5-(羟基甲基)二氢-2(3H)-呋喃酮 在 bismuth(III) bromide 、 三甲基溴硅烷 、 二乙胺基三氟化硫 、 MeOPH Jacobsen's catalyst 、 二异丁基氢化铝 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 tert-butyl-[[(2S,4S,5R)-5-(6-chloropurin-9-yl)-4-fluorooxolan-2-yl]methoxy]-diphenylsilane
  参考文献：
  名称：

  A concise synthesis of anti-viral agent F-ddA, starting from (S)-dihydro-5-(hydroxymethyl)-2(3H)-furanone

  摘要：

  Anti-HIV agent beta-F-ddA (1) has been synthesized starting from readily available non-sugar, (S)-(+)-Dihydro-5-(hydroxymethyl)-2-(3H)-furanone (4). A highly sa n-stereoselective fluorination of the hydroxy lactone 2 generates the key intermediate fluorolactone 5 in a short and concise synthetic sequence. Reduction of 5 followed by bromination generates the aglycon which is glycosylated to generate F-ddA by amination and deprotection. Steric bulk of the 5-protecting group has minimal effect on the steric course of glycosylation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02532-7

文献信息

• A concise synthesis of anti-viral agent F-ddA, starting from (S)-dihydro-5-(hydroxymethyl)-2(3H)-furanone
  作者：Anusuya Choudhury、Fuqiang Jin、Dengjin Wang、Zhe Wang、Guoyou Xu、Dieu Nguyen、John Castoro、Michael E Pierce、Pat N Confalone

  DOI：10.1016/s0040-4039(02)02532-7

  日期：2003.1

  Anti-HIV agent beta-F-ddA (1) has been synthesized starting from readily available non-sugar, (S)-(+)-Dihydro-5-(hydroxymethyl)-2-(3H)-furanone (4). A highly sa n-stereoselective fluorination of the hydroxy lactone 2 generates the key intermediate fluorolactone 5 in a short and concise synthetic sequence. Reduction of 5 followed by bromination generates the aglycon which is glycosylated to generate F-ddA by amination and deprotection. Steric bulk of the 5-protecting group has minimal effect on the steric course of glycosylation. (C) 2002 Elsevier Science Ltd. All rights reserved.