3'-Thymidyl 2-cyanoethylphosphate | 2388-45-6

• 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: 3'-Thymidyl 2-cyanoethylphosphate
• 英文别名: β-Cyanethyl-thymidin-3'-phosphat；[3']thymidylic acid mono-(2-cyano-ethyl) ester；2-cyanoethyl [(2R,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] hydrogen phosphate
• CAS: 2388-45-6
• 化学式: C₁₃H₁₈N₃O₈P
• 分子量: 375.275
• InChiKey: IHXJHCMOFYGZPK-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  158
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5’-(4,4’-二甲氧基三苯基)-3’-脱氧胸苷 2’-(2-氰乙基-N,N-二异丙基)亚磷酰胺 生成 3'-Thymidyl 2-cyanoethylphosphate
  参考文献：
  名称：

  A SOLID SUPPORT WITH A HYDROXYALLYL LINKER, FULL PARTS OF WHICH ARE POTENTIALLY REUSABLE FOR THE SYNTHESIS OF OLIGONUCLEOTIDES

  摘要：

  This paper describes a solid support with a hydroxyallyl linker that is regenerated without loss of any parts after having used for the synthesis Of nucleolides. Reproduction of the solid support can be achieved through detachment of the oligonucleotide by treatment with an organopalladium catalyst in the presence of triethylammonium acetate and subsequent methanolysis of the resulting allyl acetate.

  DOI：

  10.1081/ncn-200061909

文献信息

• Photoremovable Protecting Groups for Phosphorylation of Chiral Alcohols. Asymmetric Synthesis of Phosphotriesters of (-)-3',5'-Dimethoxybenzoin
  作者：Michael C. Pirrung、Steven W. Shuey

  DOI：10.1021/jo00093a021

  日期：1994.7

  Procedures have been developed for the preparation of dimethoxybenzoinyl (DMB) phosphate triesters that can be deprotected photochemically. These compounds can be useful in light-directed synthesis and caging. The photochemistry of a wide variety of fluorine-, oxygen-, and nitrogen-substituted benzoin acetates was examined to determine the substitution pattern in the nonacylated aromatic ring producing optimum chemical yields. Two groups, 2',3'-dimethoxybenzoin and 3',5'dimethoxybenzoin, were found to give the highest yields of the benzofuran product and were further developed for the photochemical deprotection of phosphate esters. These reactions could not be quenched, suggesting a singlet photosolvolysis mechanism. An asymmetric synthesis of 3',5'dimethoxybenzoin via the benzaldehyde cyanohydrin was developed that minimizes the number of diastereomers formed in the phosphorylation of chiral alcohols. A phosphoramidite reagent for the derivatization of alcohols was prepared and used to produce scalemic dimethoxybenzoinyl phosphate esters from pantolactone and glycerol, serine, and tyrosine derivatives. These compounds were deprotected photochemically to produce the phosphodiesters in high yield.
• A SOLID SUPPORT WITH A HYDROXYALLYL LINKER, FULL PARTS OF WHICH ARE POTENTIALLY REUSABLE FOR THE SYNTHESIS OF OLIGONUCLEOTIDES
  作者：Mamoru Hyodo、Mari Morimura、Yoshihiro Hayakawa

  DOI：10.1081/ncn-200061909

  日期：2005.4.1

  This paper describes a solid support with a hydroxyallyl linker that is regenerated without loss of any parts after having used for the synthesis Of nucleolides. Reproduction of the solid support can be achieved through detachment of the oligonucleotide by treatment with an organopalladium catalyst in the presence of triethylammonium acetate and subsequent methanolysis of the resulting allyl acetate.