5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-2'(R)-hydroxymethyl-1',3'-oxathiolane | 389128-31-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-2'(R)-hydroxymethyl-1',3'-oxathiolane
• 英文别名: 4-(4-azidobutylamino)-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
• CAS: 389128-31-8
• 化学式: C₁₂H₁₈N₆O₃S
• 分子量: 326.379
• InChiKey: IAKGWMZBQQPDLR-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-2'(R)-hydroxymethyl-1',3'-oxathiolane 在 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 10.5h， 生成 5'(R)-{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：

  5'(S)-[O4-(2,4,6-triisopropylbenzenesulfonyl)uracil-1-yl]-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.92h， 生成 5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-2'(R)-hydroxymethyl-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