(-)-(1S,3S)-3-tert-butyldimethylsilyloxymethyl-3-fluorocyclopentan-1-ol | 330805-65-7

• 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: (-)-(1S,3S)-3-tert-butyldimethylsilyloxymethyl-3-fluorocyclopentan-1-ol
• 英文别名: (1S,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-fluorocyclopentan-1-ol
• CAS: 330805-65-7
• 化学式: C₁₂H₂₅FO₂Si
• 分子量: 248.413
• InChiKey: QNFYBXUPDOOZPL-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(1S,3S)-3-tert-butyldimethylsilyloxymethyl-3-fluorocyclopentan-1-ol 在 吡啶 、 1H-1,2,4-三唑 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 氨 、 三苯基膦 、 偶氮二甲酸二乙酯 、 4-氯苯基二氯磷酸酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 (-)-1-[(1S,4S)-4-fluoro-4-hydroxymethylcyclopentan-1-yl]cytosine
  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
• 作为产物：
  描述：

  (3R)-3-tert-butyldimethylsilyloxymethyl-6-tert-butyldimethylsilyloxy-3-fluorohex-4-en-1-al 在 palladium on activated charcoal Grubbs catalyst first generation 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 4.0h， 生成 (-)-(1S,3S)-3-tert-butyldimethylsilyloxymethyl-3-fluorocyclopentan-1-ol
  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

• Synthesis and Antiretroviral Activity of Novel 4′-Fluoro-5′-Deoxyphosphonic Acid Carbocyclic Nucleoside Analogs
  作者：Eunae Kim、Seyeon Kim、Joon Hee Hong

  DOI：10.1080/15257770.2014.920506

  日期：2014.10.3

  phosphonic acid analogs with the 4′-electropositive moiety, fluorine were designed, and synthesized from glyceraldehyde. The cyclopentenol intermediate, 9, was successfully synthesized by the ring-closing metathesis of divinyl 8. The condensation reaction of cyclopentanol 15 with purine bases under Mitsunobu conditions successfully afforded the desired phosphonate analogs. The synthesized nucleoside phosphonic

  设计并合成了由甘油醛合成的具有4'-正电部分氟的新型5'-脱氧碳环嘌呤膦酸类似物。环戊烯醇中间体9通过二乙烯基8的闭环易位反应成功合成。在Mitsunobu条件下，环戊醇15与嘌呤碱的缩合反应成功得到所需的膦酸酯类似物。将合成的核苷膦酸类似物，19，22，26，和29，进行针对人免疫缺陷病毒的抗病毒筛选（HIV）-1。鸟嘌呤膦酸类似物29显示出显着的抗HIV活性（EC50 = 10.3μM）。