[(2R,3S,4S,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-cyanooxolan-3-yl] [(2R,3S,5R)-3-[bis(4-methoxyphenyl)-phenylmethoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl prop-2-enyl phosphate | 215318-36-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: [(2R,3S,4S,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-cyanooxolan-3-yl] [(2R,3S,5R)-3-[bis(4-methoxyphenyl)-phenylmethoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl prop-2-enyl phosphate
• CAS: 215318-36-8
• 化学式: C₆₇H₆₇N₆O₁₆P
• 分子量: 1243.27
• InChiKey: WVYGTQFZQCTSOE-JZPONMDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  90
• 可旋转键数：
  26
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  254
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-cyanooxolan-3-yl] [(2R,3S,5R)-3-[bis(4-methoxyphenyl)-phenylmethoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl prop-2-enyl phosphate 在 盐酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 Phosphoric acid allyl ester (2R,3S,4S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-4-cyano-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Evidence supporting the activity of 2′-C-cyano-2′-deoxy-1-β-d-arabino-pentafuranosylcytosine as a terminator in enzymatic DNA-chain elongation

  摘要：

  To investigate the stability of 2'-C-cyano-2'-deoxy-1-beta-D-arabino-pentafuranosylcytosine 3'-phosphoric acid, its thymidine ester was prepared via the phosphoramidite method using allyl protection for the phosphate function. This ester is stable under acidic conditions but extremely labile under basic conditions, decomposing with a cleavage of the internucleotide bond even at pH 7.3. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00459-4
• 作为产物：
  描述：

  3’-O-(4,4’-二甲氧基三苯甲基)胸苷 在 四氮唑 、 叔丁基过氧化氢 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 0.13h， 生成 [(2R,3S,4S,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-cyanooxolan-3-yl] [(2R,3S,5R)-3-[bis(4-methoxyphenyl)-phenylmethoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl prop-2-enyl phosphate
  参考文献：
  名称：

  Evidence supporting the activity of 2′-C-cyano-2′-deoxy-1-β-d-arabino-pentafuranosylcytosine as a terminator in enzymatic DNA-chain elongation

  摘要：

  To investigate the stability of 2'-C-cyano-2'-deoxy-1-beta-D-arabino-pentafuranosylcytosine 3'-phosphoric acid, its thymidine ester was prepared via the phosphoramidite method using allyl protection for the phosphate function. This ester is stable under acidic conditions but extremely labile under basic conditions, decomposing with a cleavage of the internucleotide bond even at pH 7.3. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00459-4

文献信息

• Ethyl(methyl)dioxirane as an Efficient Reagent for the Oxidation of Nucleoside Phosphites into Phosphates under Nonbasic Anhydrous Conditions
  作者：Masanori Kataoka、Akira Hattori、Shinya Okino、Mamoru Hyodo、Mitsue Asano、Rie Kawai、Yoshihiro Hayakawa

  DOI：10.1021/ol000364w

  日期：2001.3.1

  [GRAPHICS]A convenient method for the oxidation of nucleoside phosphites into phosphates under nonbasic and nonaqueous conditions using commercially available ethyl(methyl)dioxirane has been developed. This oxidation is effective with both N-protected and N-unprotected strategies.
• Evidence supporting the activity of 2′-C-cyano-2′-deoxy-1-β-d-arabino-pentafuranosylcytosine as a terminator in enzymatic DNA-chain elongation
  作者：Yoshihiro Hayakawa、Rie Kawai、Kaori Otsuki、Masanori Kataoka、Akira Matsuda

  DOI：10.1016/s0960-894x(98)00459-4

  日期：1998.9

  To investigate the stability of 2'-C-cyano-2'-deoxy-1-beta-D-arabino-pentafuranosylcytosine 3'-phosphoric acid, its thymidine ester was prepared via the phosphoramidite method using allyl protection for the phosphate function. This ester is stable under acidic conditions but extremely labile under basic conditions, decomposing with a cleavage of the internucleotide bond even at pH 7.3. (C) 1998 Elsevier Science Ltd. All rights reserved.