(2R,3R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-iodo-1H-indol-3-yl)-2-mercapto-butyric acid ethyl ester | 478916-49-3

• 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: (2R,3R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-iodo-1H-indol-3-yl)-2-mercapto-butyric acid ethyl ester
• CAS: 478916-49-3
• 化学式: C₂₀H₃₀INO₃SSi
• 分子量: 519.519
• InChiKey: KIWHZRWVCNJXIP-KBXCAEBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  51.32
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-iodo-1H-indol-3-yl)-2-mercapto-butyric acid ethyl ester 在 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  The antimicrobial natural product chuangxinmycin and Some synthetic analogues are potent and selective inhibitors of bacterial tryptophanyl tRNA synthetase

  摘要：

  The antimicrobial natural product chuangxinmycin has been found to be a potent and selective inhibitor of bacterial tryptophanyl tRNA synthetase (WRS). A number of analogues have been synthesised. The interaction with WRS appears to be highly constrained, as only sterically smaller analogues afforded significant inhibition. The only analogue to show inhibition comparable to chuangxinmycin also had antibacterial activity. WRS inhibition may contribute to the antibacterial action of chuangxinmycin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00604-2
• 作为产物：
  描述：

  (2R,3S)-2,3-epoxy-4-(tert-butyldimethylsilyloxy)-butanoic acid ethyl ester 在 吡啶 、 四氯化锡 、 potassium carbonate 、 三乙胺 、 1,4-二巯基-2,3-丁二醇 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-iodo-1H-indol-3-yl)-2-mercapto-butyric acid ethyl ester
  参考文献：
  名称：

  The antimicrobial natural product chuangxinmycin and Some synthetic analogues are potent and selective inhibitors of bacterial tryptophanyl tRNA synthetase

  摘要：

  The antimicrobial natural product chuangxinmycin has been found to be a potent and selective inhibitor of bacterial tryptophanyl tRNA synthetase (WRS). A number of analogues have been synthesised. The interaction with WRS appears to be highly constrained, as only sterically smaller analogues afforded significant inhibition. The only analogue to show inhibition comparable to chuangxinmycin also had antibacterial activity. WRS inhibition may contribute to the antibacterial action of chuangxinmycin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00604-2