1-<2',3'-dideoxy-3'-C-(hydroxymethyl)-α-D-erythro-pentofuranosyl>cytosine | 132235-72-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-<2',3'-dideoxy-3'-C-(hydroxymethyl)-α-D-erythro-pentofuranosyl>cytosine
• 英文别名: 1-[2',3'-dideoxy-3'-C-(hydroxymethyl)-α-D-erythro-pentofuranosyl]cytosine；4-amino-1-[(2S,4R,5S)-4,5-bis(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 132235-72-4
• 化学式: C₁₀H₁₅N₃O₄
• 分子量: 241.247
• InChiKey: WZGBNAXNHRMYLG-BHNWBGBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 盐酸 、 sodium periodate 、 氨 、 sodium 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 1.17h， 生成 1-<2',3'-dideoxy-3'-C-(hydroxymethyl)-α-D-erythro-pentofuranosyl>cytosine
  参考文献：
  名称：

  Synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides as potential inhibitors of HIV

  摘要：

  A novel synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides is described. (2S,3R)-3-[[(4-Bromobenzyl)oxy]methyl]oxirane-2-methanol (1) was regioselectively alkylated using allylmagnesium bromide. The allyl double bond was oxidatively cleaved, and the product was treated with acidic methanol to give the requisite methyl furanoside derivative 5, which was subsequently condensed with purine and pyrimidine bases. Deblocking and separation of the anomers by chromatography afforded the alpha- and beta-nucleoside analogues.

  DOI：

  10.1021/jo00009a012

文献信息

• Mann, John; Weymouth-Wilson, Alexander C., Journal of the Chemical Society. Perkin transactions I, 1994, # 21, p. 3141 - 3148
  作者：Mann, John、Weymouth-Wilson, Alexander C.

  DOI：——

  日期：——
• SVANSSON, LARS;KVARNSTROM, INGEMAR;CLASSON, BJORN;SAMUELSSON, BERTIL, J. ORG. CHEM., 56,(1991) N, C. 2993-2997
  作者：SVANSSON, LARS、KVARNSTROM, INGEMAR、CLASSON, BJORN、SAMUELSSON, BERTIL

  DOI：——

  日期：——
• Synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides as potential inhibitors of HIV
  作者：Lars Svansson、Ingemar Kvarnstroem、Bjoern Classon、Bertil Samuelsson

  DOI：10.1021/jo00009a012

  日期：1991.4

  A novel synthesis of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides is described. (2S,3R)-3-[[(4-Bromobenzyl)oxy]methyl]oxirane-2-methanol (1) was regioselectively alkylated using allylmagnesium bromide. The allyl double bond was oxidatively cleaved, and the product was treated with acidic methanol to give the requisite methyl furanoside derivative 5, which was subsequently condensed with purine and pyrimidine bases. Deblocking and separation of the anomers by chromatography afforded the alpha- and beta-nucleoside analogues.