(Z)-5-{[(2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-bis-triethylsilanyloxy-tetrahydro-furan-2-ylmethyl]-amino}-4-bromo-pent-3-enoic acid ethyl ester | 740817-85-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: (Z)-5-{[(2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-bis-triethylsilanyloxy-tetrahydro-furan-2-ylmethyl]-amino}-4-bromo-pent-3-enoic acid ethyl ester
• 英文别名: ethyl (Z)-5-[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]methylamino]-4-bromopent-3-enoate
• CAS: 740817-85-0
• 化学式: C₂₉H₅₁BrN₆O₅Si₂
• 分子量: 699.836
• InChiKey: DYOIGCOLLCJXGU-AHVZRTQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  43
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (Z)-5-{[(2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-bis-triethylsilanyloxy-tetrahydro-furan-2-ylmethyl]-amino}-4-bromo-pent-3-enoic acid ethyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到(E)-3-{1-[(2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-bis-triethylsilanyloxy-tetrahydro-furan-2-ylmethyl]-aziridin-2-yl}-acrylic acid ethyl ester
  参考文献：
  名称：

  Aziridination of γ,δ-dibromoethyl-2-pentenoate with primary amines: extension of the Gabriel–Cromwell reaction

  摘要：

  Ethyl (E)-4,5-dibromo-2-pentenoate readily reacts with an assortment of primary amines in the presence of DBU to afford the corresponding conjugated aziridines in good to moderate yields. That the reaction is compatible with a nucleoside-derived amine suggests a broad scope of application. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.005
• 作为产物：
  描述：

  (S)-(+)-3-(2,2-二甲基-1,3-二氧戊环-4-基)-反式-丙酸乙酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-5-{[(2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-3,4-bis-triethylsilanyloxy-tetrahydro-furan-2-ylmethyl]-amino}-4-bromo-pent-3-enoic acid ethyl ester
  参考文献：
  名称：

  Aziridination of γ,δ-dibromoethyl-2-pentenoate with primary amines: extension of the Gabriel–Cromwell reaction

  摘要：

  Ethyl (E)-4,5-dibromo-2-pentenoate readily reacts with an assortment of primary amines in the presence of DBU to afford the corresponding conjugated aziridines in good to moderate yields. That the reaction is compatible with a nucleoside-derived amine suggests a broad scope of application. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.005

文献信息

• Aziridination of γ,δ-dibromoethyl-2-pentenoate with primary amines: extension of the Gabriel–Cromwell reaction
  作者：Rachel L. Weller、Scott R. Rajski

  DOI：10.1016/j.tetlet.2004.06.005

  日期：2004.7

  Ethyl (E)-4,5-dibromo-2-pentenoate readily reacts with an assortment of primary amines in the presence of DBU to afford the corresponding conjugated aziridines in good to moderate yields. That the reaction is compatible with a nucleoside-derived amine suggests a broad scope of application. (C) 2004 Elsevier Ltd. All rights reserved.