N⁴-acetyl-1-<2-C-cyano-2-deoxy-5-O-(dimethoxytrityl)-β-D-arabinofuranosyl>cytosine | 140859-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N⁴-acetyl-1-<2-C-cyano-2-deoxy-5-O-(dimethoxytrityl)-β-D-arabinofuranosyl>cytosine
• 英文别名: N-[1-[(2R,3S,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-cyano-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
• CAS: 140859-05-8
• 化学式: C₃₃H₃₂N₄O₇
• 分子量: 596.64
• InChiKey: QAQJRTSUDBDQEI-MAJIKDHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N⁴-acetyl-1-<2-C-cyano-2-deoxy-5-O-(dimethoxytrityl)-β-D-arabinofuranosyl>cytosine 在 四氮唑 、 邻苯二甲酸二甲酯 、 ethylmethyldioxirane 作用下， 以 二氯甲烷 为溶剂， 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：

  Ethyl(methyl)dioxirane as an Efficient Reagent for the Oxidation of Nucleoside Phosphites into Phosphates under Nonbasic Anhydrous Conditions

  摘要：

  [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.

  DOI：

  10.1021/ol000364w
• 作为产物：
  描述：

  N⁴-acetyl-1-<3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-erythro-pentofuran-2-ulosyl>cytosine 在 吡啶 、 4-二甲氨基吡啶 、 phosphate buffer 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 、 乙腈 为溶剂， 反应 8.75h， 生成 N⁴-acetyl-1-<2-C-cyano-2-deoxy-5-O-(dimethoxytrityl)-β-D-arabinofuranosyl>cytosine
  参考文献：
  名称：

  Azuma; Nakajima; Nishizono, Journal of Medicinal Chemistry, 1993, vol. 36, # 26, p. 4183 - 4189

  摘要：

  DOI：

文献信息

• 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.
• Nucleosides and nucleotides. 100. 2'-C-Cyano-2'-deoxy-1-.beta.-D-arabinofuranosylcytosine (CNDAC): design of a potential mechanism-based DNA-strand-breaking antineoplastic nucleoside
  作者：Akira Matsuda、Yuki Nakajima、Atsushi Azuma、Motohiro Tanaka、Takuma Sasaki

  DOI：10.1021/jm00113a034

  日期：1991.9
• 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.
• Azuma; Nakajima; Nishizono, Journal of Medicinal Chemistry, 1993, vol. 36, # 26, p. 4183 - 4189
  作者：Azuma、Nakajima、Nishizono、Minakawa、Suzuki、Hanaoka、Kobayashi、Tanaka、Sasaki、Matsuda

  DOI：——

  日期：——