(3S,4S)-3,4-bis[[tert-butyl(diphenyl)silyl]oxymethyl]cyclopentan-1-one | 141389-79-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3S,4S)-3,4-bis[[tert-butyl(diphenyl)silyl]oxymethyl]cyclopentan-1-one
• CAS: 141389-79-9
• 化学式: C₃₉H₄₈O₃Si₂
• 分子量: 620.979
• InChiKey: YJHGSFBMTAGOQD-ROJLCIKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.73
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3,4-bis[[tert-butyl(diphenyl)silyl]oxymethyl]cyclopentan-1-one 在 Selectfluor 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.5h， 生成 (3S,4S)-3,4-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-2-fluoro-cyclopentanone
  参考文献：
  名称：

  碳环2'3'-二脱氧-2'-氟-3'-C-羟甲基核苷类似物的合成作为HIV和HSV的潜在抑制剂

  摘要：

  描述了四种异构纯的氟碳环腺苷和鸟苷类似物的合成。3小号，4小号双（吨-butyldiphenylsilyoxymethyl）-2- fluoropentan -1-醇衍生物22，23，24和25从对映异构纯3中合成小号，4小号双（吨-butyldiphenyl-silyloxymethyl） -环戊酮（ bd18）与氯嘌呤结合，使用Mitsunobu程序得到10、11、12、14和16或转化为它们相应的1-氨基衍生物，氟碳鸟嘌呤类似物13、15和17准备好了。化合物10-17被评估为潜在的抗病毒药，但被发现没有活性。

  DOI：

  10.1016/s0040-4020(96)01103-9
• 作为产物：
  描述：

  trans-3,4-bis(hdroxymethyl)cyclopentanone ethylene acetal 在 吡啶 、 溶剂黄146 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 62.0h， 生成 (3S,4S)-3,4-bis[[tert-butyl(diphenyl)silyl]oxymethyl]cyclopentan-1-one
  参考文献：
  名称：

  Synthesis of 3′,4′-C-Bishydroxymethyl-2′,3′,4′-trideoxy-β-L-threo-pentopyranosyl Nucleosides as Potential Inhibitors of HIV

  摘要：

  The synthesis of 3',4'-bishydroxymethy1-2',3',4'-trideoxy pentopyranosyl derivatives of thymine, uracil, cytosine, and adenine is described. trans-(3S, 4S)-Bis (methoxycarbonyl)cyclopentanone (3) as converted to 1-O-acetyl-3,4-C-bis[(tert-butyldiphenylsiloxy)methyl] -2,3,4-trideoxy-alpha,beta-L-threo-pentopyranose (6), which was subsequently condensed with the silylated purine and pyrimidine bases.

  DOI：

  10.1080/15257779508009487

文献信息

• Synthesis of carbocyclic 2′3′-dideoxy-2′-fluoro-3′-C-hydroxymethyl nucleoside analogues as potential inhibitors of HIV and HSV
  作者：Johanna Wachtmeister、Classon Björn、Samuelsson Bertil、Ingemar Kvarnström

  DOI：10.1016/s0040-4020(96)01103-9

  日期：1997.2

  The synthesis of four isomerically pure fluoro-carbocyclic adenosine and guanosine analogues is described. The 3S, 4S-bis(t-butyldiphenylsilyoxymethyl)-2-fluoropentan-1-ol derivatives 22, 23, 24 and 25 synthesized from enantiomerically pure 3S, 4S-bis(t-butyldiphenyl-silyloxymethyl)-cyclopentanone (bd18), were coupled with chloropurines using the Mitsunobu procedure to give 10, 11, 12, 14 and 16 or

  描述了四种异构纯的氟碳环腺苷和鸟苷类似物的合成。3小号，4小号双（吨-butyldiphenylsilyoxymethyl）-2- fluoropentan -1-醇衍生物22，23，24和25从对映异构纯3中合成小号，4小号双（吨-butyldiphenyl-silyloxymethyl） -环戊酮（ bd18）与氯嘌呤结合，使用Mitsunobu程序得到10、11、12、14和16或转化为它们相应的1-氨基衍生物，氟碳鸟嘌呤类似物13、15和17准备好了。化合物10-17被评估为潜在的抗病毒药，但被发现没有活性。
• Synthesis of 2′,3′-dideoxycyclo-2′-pentenyl-3′-C-hydroxymethyl carbocyclic nucleoside analogues as potential anti-viral agents
  作者：Johanna Wachtmeister、Björn Classon、Bertil Samuelsson、Ingmar Kvarnström

  DOI：10.1016/0040-4020(94)01067-a

  日期：1995.2

  The synthesis of optically pure unsaturated carbocyclic nucleoside analogues is described. (3,4S)-Bis(t-butyldiphenylsilyloxymethyl)-2-cyclopenten-1R and 1S-ol were coupled with 6-chloropurine and 2-amino-6-chloropurine respectively, using a modified Mitsunobu reaction. The products were reacted further using standard procedures to give compounds 12, 14, 16 and 18 which were tested for anti-HIV activity

  描述了光学纯的不饱和碳环核苷类似物的合成。（3,4-小号） -双（吨-butyldiphenylsilyloxymethyl）-2-环戊烯-1- [R和1个小号醇分别与6-氯嘌呤和2-氨基-6-氯嘌呤，使用改良的Mitsunobu反应。使用标准程序使产物进一步反应，得到化合物12、14、16和18，其经测试具有抗HIV活性。
• Synthesis of Novel Olefinic Carbocyclic Purine Nucleoside Analogues
  作者：Johanna Wachtmeister、Bjorn Classon、Bertil Samuelsson、Ingemar Kvarnström

  DOI：10.1080/15257779508012395

  日期：1995.5.1

  The synthesis of optically pure unsaturated carbocyclic nucleoside analogues is described. (3,4S)-Bis(t-butyldiphenyl silyloxymethyl)-1R and 1S cyclopent-2-en-1-ol were coupled with 6-chloropurine and 2-amino-6-chloropurine respectively, using a modified Mitsunobu reaction. The products were reacted further using standard procedures to give compounds 12, 14, 16 and 18.
• Synthesis of Novel Fluoro Carbocyclic Purine Nucleoside Analogues
  作者：Johanna Wachtmeister、Björn Classon、Ingemar Kvarnströmn、Bertil Samuelsson

  DOI：10.1080/07328319708002956

  日期：1997.5

  The synthesis of four isomer isomerically pure fluoro-carbocyclic adenosine and guanosine analogues is described.
• Synthesis of 3′,4′-C-Bishydroxymethyl-2′,3′,4′-trideoxy-β-L-threo-pentopyranosyl Nucleosides as Potential Inhibitors of HIV
  作者：Åsa Lundquist、Ingemar Kvarnström、Stefan C. T. Svensson、Björn Classon、Bertil Samuelsson

  DOI：10.1080/15257779508009487

  日期：1995.9

  The synthesis of 3',4'-bishydroxymethy1-2',3',4'-trideoxy pentopyranosyl derivatives of thymine, uracil, cytosine, and adenine is described. trans-(3S, 4S)-Bis (methoxycarbonyl)cyclopentanone (3) as converted to 1-O-acetyl-3,4-C-bis[(tert-butyldiphenylsiloxy)methyl] -2,3,4-trideoxy-alpha,beta-L-threo-pentopyranose (6), which was subsequently condensed with the silylated purine and pyrimidine bases.