4-(3-tert-butoxycarbonylamino-3-methoxycarbonyl-propylsulfanylmethyl)-6-[1-cyano-2-(cyanomethyl-amino)-vinyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester | 875670-78-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(3-tert-butoxycarbonylamino-3-methoxycarbonyl-propylsulfanylmethyl)-6-[1-cyano-2-(cyanomethyl-amino)-vinyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester
• CAS: 875670-78-3
• 化学式: C₂₈H₄₃N₅O₈S
• 分子量: 609.744
• InChiKey: GCGPMLBAHOXJMI-PPGORRQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  172.24
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4-(3-tert-butoxycarbonylamino-3-methoxycarbonyl-propylsulfanylmethyl)-6-[1-cyano-2-(cyanomethyl-amino)-vinyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester 在 敌草腈 、 sodium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 4-(4-amino-5-cyano-1H-pyrrol-3-yl)-6-(3-tert-butoxycarbonylamino-3-methoxycarbonyl-propylsulfanylmethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of a potent 5′-methylthioadenosine/S-adenosylhomocysteine (MTAN) inhibitor

  摘要：

  MTAN has been known to occur in a variety of bacterial cell types. Due to the evolution of bacterial strains which are resistant to some of the most powerful antibiotics there has been a renewed interest in the development of novel anti-microbial agents. Presented herein is a synthesis of a potent MTAN inhibitor, namely 2-amino-4-[5-(4-amino-5H-pyrrolo[3,2-d]pyrimidin7-yl)-3,4-dihydroxypyrrolidin-2-ylmethylsulfanyl]-butyric acid (1). (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.029
• 作为产物：
  描述：

  1-氮杂二环[2.2.1]庚烷,3-(氨基氧代)-,内-(9CI) 在 4-二甲氨基吡啶 、 sodium acetate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 4-(3-tert-butoxycarbonylamino-3-methoxycarbonyl-propylsulfanylmethyl)-6-[1-cyano-2-(cyanomethyl-amino)-vinyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of a potent 5′-methylthioadenosine/S-adenosylhomocysteine (MTAN) inhibitor

  摘要：

  MTAN has been known to occur in a variety of bacterial cell types. Due to the evolution of bacterial strains which are resistant to some of the most powerful antibiotics there has been a renewed interest in the development of novel anti-microbial agents. Presented herein is a synthesis of a potent MTAN inhibitor, namely 2-amino-4-[5-(4-amino-5H-pyrrolo[3,2-d]pyrimidin7-yl)-3,4-dihydroxypyrrolidin-2-ylmethylsulfanyl]-butyric acid (1). (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.029