Diethyl 2',3'-O-isopropylideneadenosine 5'-phosphate | 89560-37-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: Diethyl 2',3'-O-isopropylideneadenosine 5'-phosphate
• 英文别名: [(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl diethyl phosphate
• CAS: 89560-37-2
• 化学式: C₁₇H₂₆N₅O₇P
• 分子量: 443.396
• InChiKey: JDDDKDNAUFDRHS-XNIJJKJLSA-N

物化性质

• 沸点：
  613.3±65.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2',3'-异丙叉腺苷 、 氯磷酸二乙酯 在 LiAl(NMe₂)4 、 邻氯苯酚 作用下， 生成 Diethyl 2',3'-O-isopropylideneadenosine 5'-phosphate
  参考文献：
  名称：

  Chemoselective phosphorylation of -unprotected nucleosides via aluminum alkoxides

  摘要：

  DOI：

  10.1016/s0040-4039(00)94162-5

文献信息

• Synthesis of adenosine-5′-phosphates and 5′-alkylphosphonates via the Mitsunobu reaction
  作者：Mourad Saady、Luc Lebeau、Charles Mioskowski

  DOI：10.1016/0040-4039(95)00234-4

  日期：1995.3

  The Mitsunobu reaction can be successfully applied to achieve phosphorylation and phosphonylation of purine nucleosides. A series of different adenosine-5′-phosphate analogs was obtained with good to excellent yields.

  Mitsunobu反应可以成功地用于实现嘌呤核苷的磷酸化和膦酰化。获得了一系列不同的具有良好至优异产率的不同的腺苷-5'-磷酸类似物。
• O-selective phosphorylation of nucleosides without N-protection
  作者：Mamoru Uchiyama、Yoshio Aso、Ryoji Noyori、Yoshihiro Hayakawa

  DOI：10.1021/jo00054a020

  日期：1993.1

  A facile chemoselective O-phosphorylation of N-unprotected nucleosides has been achieved via metal alkoxide formation. Sequential treatment of N-unprotected nucleosides with an equimolar amount of a metallo-organic base such as an alkyllithium, potassium tert-butoxide, tert-butylmagnesium chloride, LiAl[N(CH3)2]4, Al[N(CH3)2]3, (i-C4H9)2AlH, etc., and a phosphorochloridate or p-nitrophenyl phosphate results in rapid O-phosphorylation to give the corresponding nucleotides in high yield. The method using magnesium alkoxides is among the best, considering its chemoselectivity, generality, and operational simplicity. The origin of the observed chemoselectivity is discussed.