Diethyl 5'-O-(tert-butyldimethylsilyl)thymidine 3'-phosphate | 89539-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: Diethyl 5'-O-(tert-butyldimethylsilyl)thymidine 3'-phosphate
• 英文别名: [(2R,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] diethyl phosphate
• CAS: 89539-18-4
• 化学式: C₂₀H₃₇N₂O₈PSi
• 分子量: 492.582
• InChiKey: ZPZBIMLXXYTDCF-GVDBMIGSSA-N

物化性质

• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  氯磷酸二乙酯 、 5’-O-(叔丁基二甲基甲硅烷基)胸苷 在 叔丁基氯化镁 作用下， 生成 Diethyl 5'-O-(tert-butyldimethylsilyl)thymidine 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

• Indolyl-oxazaphosphorine Precursors for Stereoselective Synthesis of Phosphite Triesters and Dithymidinyl Phosphorothioates
  作者：Jian-Chao Wang、George Just

  DOI：10.1021/jo990242l

  日期：1999.10.1

  7 were synthesized, and their potential as precursors to chiral phosphorothioates was evaluated. Reaction of 7 with a thymidine derivative gave phosphite triester 8 with a large degree of stereoselectivity. Sulfurization with Beaucage's reagent provided phosphorothioate triesters 9. The chiral auxiliary 9b containing a cyano group could be easily removed with aqueous ammonia to form dithymidinyl phosphorothioate

  合成了几种新颖的手性吲哚基-氧杂氮杂膦7，并评估了它们作为手性硫代磷酸酯的前体的潜力。7与胸腺嘧啶衍生物的反应产生了具有高度立体选择性的亚磷酸三酯8。用Beaucage试剂进行硫化可提供硫代磷酸酯三酯9。含有氰基的手性助剂9b可以很容易地用氨水除去，形成过量97％非对映异构体的硫代二嘧啶基硫代磷酸酯。手性吲哚基-氧杂氮杂膦7是用于硫代磷酸酯的立体选择性合成的新型前体。
• Chemoselective phosphorylation of -unprotected nucleosides via aluminum alkoxides
  作者：Y. Hayakawa、Y. Aso、M. Uchiyama、R. Noyori

  DOI：10.1016/s0040-4039(00)94162-5

  日期：1983.1