5'(S)-{N4-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester | 389128-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5'(S)-{N4-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester
• 英文别名: 5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester
• CAS: 389128-30-7
• 化学式: C₂₂H₃₄N₆O₄S
• 分子量: 478.616
• InChiKey: LOUCIWGAUUCBLB-AJBNAHFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  131.21
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5'(S)-{N4-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester 在 lithium aluminium tetrahydride 、 正丁基锂 、 三甲基溴硅烷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 10.67h， 生成 5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-2'(R)-dihydroxyphosphoryloxymethyl-1',3'-oxathiolane
  参考文献：
  名称：

  Synthesis of haptens for the development of immunoassays for the monitoring of intracellular anti-HIV nucleosides and nucleotides

  摘要：

  A series of nine modified dideoxynucleosides and dideoxynucleotides has been synthesized for preparing antigenic conjugates with keyhole lympet haemocyanin in order to produce specific antibodies, and develop immunoassays. Derivatives of ddI, ddA, d4T, 3TC, and the corresponding 5 ' -O-monophosphates were designed incorporating an amino spacer at the base for conjugation with the proteinic antigenic carrier. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00800-6
• 作为产物：
  描述：

  拉米夫定杂质27 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.75h， 生成 5'(S)-{N4-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester
  参考文献：
  名称：

  Synthesis of haptens for the development of immunoassays for the monitoring of intracellular anti-HIV nucleosides and nucleotides

  摘要：

  A series of nine modified dideoxynucleosides and dideoxynucleotides has been synthesized for preparing antigenic conjugates with keyhole lympet haemocyanin in order to produce specific antibodies, and develop immunoassays. Derivatives of ddI, ddA, d4T, 3TC, and the corresponding 5 ' -O-monophosphates were designed incorporating an amino spacer at the base for conjugation with the proteinic antigenic carrier. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00800-6