(1R*,4S*)-cis-4-t-butyldimethylsilyloxy-2-cyclopentenyl diethylphosphate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (1R*,4S*)-cis-4-t-butyldimethylsilyloxy-2-cyclopentenyl diethylphosphate
• 英文别名: [(1R,4S)-4-[tert-butyl(dimethyl)silyl]oxycyclopent-2-en-1-yl] diethyl phosphate
• 化学式: C₁₅H₃₁O₅PSi
• 分子量: 350.467
• InChiKey: RLLJWBQEBMHMAF-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  腺嘌呤 、 (1R*,4S*)-cis-4-t-butyldimethylsilyloxy-2-cyclopentenyl diethylphosphate 在 四(三苯基膦)钯 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以5%的产率得到7N-<(1'S*,4'R*)-cis-(4'-t-butyldimethylsilyloxy)cyclopent-2'-enyl> adenine
  参考文献：
  名称：

  An Unanticipated Result in the Pd (0) Catalyzed Coupling of Sodium Adenate withcis-4-Acetyloxy- andcis-4-t-Butyldimethylsilyloxy-2-Cyclopentenyl Diethylphosphate

  摘要：

  The preparation of adenine regioisomers of (+/-)-cis-4-(TBSO)- and (+/-)-cis-4-(AcO)-2-cyclopentene is described using either Pd(0) coupling (silyl ether 2) or chloride displacement (acetyl chloride 10). An unexpected difference in reactivity between TBS- and Ac-O-protected allyl phosphates 2 and 7 in Pd(0) catalyzed coupling with sodium adenate was observed.

  DOI：

  10.1080/00397919608003730
• 作为产物：
  描述：

  氯磷酸二乙酯 、 2-环戊烯-1-醇,4-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]-,(1R,4S)- 在 咪唑 作用下， 以 乙腈 为溶剂， 反应 7.0h， 以55%的产率得到(1R*,4S*)-cis-4-t-butyldimethylsilyloxy-2-cyclopentenyl diethylphosphate
  参考文献：
  名称：

  An Unanticipated Result in the Pd (0) Catalyzed Coupling of Sodium Adenate withcis-4-Acetyloxy- andcis-4-t-Butyldimethylsilyloxy-2-Cyclopentenyl Diethylphosphate

  摘要：

  The preparation of adenine regioisomers of (+/-)-cis-4-(TBSO)- and (+/-)-cis-4-(AcO)-2-cyclopentene is described using either Pd(0) coupling (silyl ether 2) or chloride displacement (acetyl chloride 10). An unexpected difference in reactivity between TBS- and Ac-O-protected allyl phosphates 2 and 7 in Pd(0) catalyzed coupling with sodium adenate was observed.

  DOI：

  10.1080/00397919608003730

文献信息

• An Unanticipated Result in the Pd (0) Catalyzed Coupling of Sodium Adenate with<i>cis</i>-4-Acetyloxy- and<i>cis</i>-4-<i>t</i>-Butyldimethylsilyloxy-2-Cyclopentenyl Diethylphosphate
  作者：Timothy T. Curran

  DOI：10.1080/00397919608003730

  日期：1996.3

  The preparation of adenine regioisomers of (+/-)-cis-4-(TBSO)- and (+/-)-cis-4-(AcO)-2-cyclopentene is described using either Pd(0) coupling (silyl ether 2) or chloride displacement (acetyl chloride 10). An unexpected difference in reactivity between TBS- and Ac-O-protected allyl phosphates 2 and 7 in Pd(0) catalyzed coupling with sodium adenate was observed.