(2S,3R)-(-)-N-(tert-butoxycarbonyl)-O-tert-butyl-2,3-methanomethionine | 143122-77-4

• 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: (2S,3R)-(-)-N-(tert-butoxycarbonyl)-O-tert-butyl-2,3-methanomethionine
• 英文别名: tert-butyl (1S,2R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(methylsulfanylmethyl)cyclopropane-1-carboxylate
• CAS: 143122-77-4
• 化学式: C₁₅H₂₇NO₄S
• 分子量: 317.45
• InChiKey: KXFACRNSHKPHFH-BONVTDFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-(-)-N-(tert-butoxycarbonyl)-O-tert-butyl-2,3-methanomethionine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到(2S,3R)-(-)-2,3-methanomethionine
  参考文献：
  名称：

  Asymmetric syntheses of all four stereoisomers of 2,3-methanomethionine

  摘要：

  Asymmetric syntheses of all four stereoisomers of 2,3-methanomethionine ((Z)- and (E)-cyclo-Met) are described. The source of chirality in these reactions is the trifluoromethylsulfonate ester 1b which reacts with di-tert-butyl malonate via direct displacement of trifluoromethylsulfonate followed by lactonization to give 1-(tert-butoxycarbonyl)-2-oxo-3-oxabicyclo[3.1.0]hexane (2). Conversion of compound 2 into (Z)-cyclo-Met can be achieved via ring opening of the lactone, Hoffmann rearrangement, mesylation, and displacement with thiomethoxide. A route to (E)-cyclo-Met was developed using a lipase to effect a critical ester hydrolysis.

  DOI：

  10.1021/jo00048a028
• 作为产物：
  描述：

  (1S,2R)-(-)-tert-butyl 2-(acetoxymethyl)-1-cyclopropane-1-carboxylate 在 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.83h， 生成 (2S,3R)-(-)-N-(tert-butoxycarbonyl)-O-tert-butyl-2,3-methanomethionine
  参考文献：
  名称：

  Asymmetric syntheses of all four stereoisomers of 2,3-methanomethionine

  摘要：

  Asymmetric syntheses of all four stereoisomers of 2,3-methanomethionine ((Z)- and (E)-cyclo-Met) are described. The source of chirality in these reactions is the trifluoromethylsulfonate ester 1b which reacts with di-tert-butyl malonate via direct displacement of trifluoromethylsulfonate followed by lactonization to give 1-(tert-butoxycarbonyl)-2-oxo-3-oxabicyclo[3.1.0]hexane (2). Conversion of compound 2 into (Z)-cyclo-Met can be achieved via ring opening of the lactone, Hoffmann rearrangement, mesylation, and displacement with thiomethoxide. A route to (E)-cyclo-Met was developed using a lipase to effect a critical ester hydrolysis.

  DOI：

  10.1021/jo00048a028