Diethyl 5'-O-(tert-butyldimethylsilyl)-N⁶,N⁶-diethyl-2'-deoxyadenosine 3'-phosphate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核糖核苷3'-磷酸盐
• 英文名称: Diethyl 5'-O-(tert-butyldimethylsilyl)-N⁶,N⁶-diethyl-2'-deoxyadenosine 3'-phosphate
• 英文别名: [(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-[6-(diethylamino)purin-9-yl]oxolan-3-yl] diethyl phosphate
• 化学式: C₂₄H₄₄N₅O₆PSi
• 分子量: 557.703
• InChiKey: ABAHDYXYXVVXMY-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine 在 四氮唑 、 叔丁基氯化镁 、 三乙胺 作用下， 反应 6.0h， 生成 Diethyl 5'-O-(tert-butyldimethylsilyl)-N⁶,N⁶-diethyl-2'-deoxyadenosine 3'-phosphate
  参考文献：
  名称：

  O-selective phosphorylation of nucleosides without N-protection

  摘要：

  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.

  DOI：

  10.1021/jo00054a020

文献信息

• 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.