ethyl (1RS,3R)-3-tert-butyldimethylsilyloxymethyl-3-fluorocyclopentan-1-yl carboxylate | 279674-91-8

• 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: ethyl (1RS,3R)-3-tert-butyldimethylsilyloxymethyl-3-fluorocyclopentan-1-yl carboxylate
• 英文别名: ethyl (1S,3R)-3-{[(tert-butyldimethylsilyl)oxy]methyl}-3-fluorocyclopentane-1-carboxylate；ethyl (3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-fluorocyclopentane-1-carboxylate
• CAS: 279674-91-8
• 化学式: C₁₅H₂₉FO₃Si
• 分子量: 304.477
• InChiKey: WLAPZDFKHZWPBP-WPZCJLIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (1RS,3R)-3-tert-butyldimethylsilyloxymethyl-3-fluorocyclopentan-1-yl carboxylate 在 lead(IV) acetate 、 sodium hydroxide 、 碳酸氢钠 作用下， 以 四氯化碳 、 六甲基磷酰三胺 、 乙醇 、 水 为溶剂， 反应 7.25h， 生成 (+)-(1S,3R)-3-tert-butyldimethylsilyloxymethyl-3-fluorocyclopentan-1-ol
  参考文献：
  名称：

  Stereoselective Synthesis of Carbocyclic l-4‘-Fluoro-2‘,3‘-dideoxyadenosine

  摘要：

  L-(1'S,3'S)-9-[3-Fluoro-3-(hydroxymethyl)cyclopentan-1-yl]adenine 15 has been synthesized from ester 2, which can be conveniently prepared from 2,3-isopropylidene-D-glyceraldehyde 1 in six steps. The key ring closure has been accomplished through an intramolecular nucleophilic substitution reaction.

  DOI：

  10.1021/ol005665k
• 作为产物：
  描述：

  (+)-(3R)-3-tert-butyldimethylsilyloxymethyl-6-tert-butyldimethylsilyloxy-3-fluorohex-4-en-1-ol 在 palladium on activated charcoal 吡啶 、 氢气 、 sodium hexamethyldisilazane 、 sodium hydride 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 环己烷 为溶剂， 反应 53.5h， 生成 ethyl (1RS,3R)-3-tert-butyldimethylsilyloxymethyl-3-fluorocyclopentan-1-yl carboxylate
  参考文献：
  名称：

  A divergent synthesis of d - and l -carbocyclic 4′-fluoro-2′,3′-dideoxynucleosides as potential antiviral agents

  摘要：

  D- and L-Carbocyclic 4'-fluoro-2',3'-dideoxynucleosides have been synthesized from 2, which can be conveniently prepared from 1.2:5.6-di-O-isopropylidene-D-mannitol 1 in eight steps. Ruthenium-catalyzed ring-closing metathesis has been employed in the synthesis of D-nucleosides, whereas the L-series have been obtained through an intramolecular nucleophilic substitution reaction. The Mitsunobu condensation was used as a general tool for the synthesis of both purine and pyrimidine nucleosides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00482-1

文献信息

• Stereoselective Synthesis of Carbocyclic <scp>l</scp>-4‘-Fluoro-2‘,3‘-dideoxyadenosine
  作者：Giuseppe Gumina、Youhoon Chong、Yongseok Choi、Chung K. Chu

  DOI：10.1021/ol005665k

  日期：2000.5.1

  L-(1'S,3'S)-9-[3-Fluoro-3-(hydroxymethyl)cyclopentan-1-yl]adenine 15 has been synthesized from ester 2, which can be conveniently prepared from 2,3-isopropylidene-D-glyceraldehyde 1 in six steps. The key ring closure has been accomplished through an intramolecular nucleophilic substitution reaction.
• A divergent synthesis of d - and l -carbocyclic 4′-fluoro-2′,3′-dideoxynucleosides as potential antiviral agents
  作者：Youhoon Chong、Giuseppe Gumina、Chung K. Chu

  DOI：10.1016/s0957-4166(00)00482-1

  日期：2000.12

  D- and L-Carbocyclic 4'-fluoro-2',3'-dideoxynucleosides have been synthesized from 2, which can be conveniently prepared from 1.2:5.6-di-O-isopropylidene-D-mannitol 1 in eight steps. Ruthenium-catalyzed ring-closing metathesis has been employed in the synthesis of D-nucleosides, whereas the L-series have been obtained through an intramolecular nucleophilic substitution reaction. The Mitsunobu condensation was used as a general tool for the synthesis of both purine and pyrimidine nucleosides. (C) 2001 Elsevier Science Ltd. All rights reserved.