Methanesulfonic acid (1R,2R)-2-tert-butoxycarbonylamino-2-cyano-cyclopropylmethyl ester | 143122-81-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Methanesulfonic acid (1R,2R)-2-tert-butoxycarbonylamino-2-cyano-cyclopropylmethyl ester
• 英文别名: [(1R,2R)-2-cyano-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropyl]methyl methanesulfonate
• CAS: 143122-81-0
• 化学式: C₁₁H₁₈N₂O₅S
• 分子量: 290.34
• InChiKey: RIGJVXCAFVJWSR-KWQFWETISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (1R,2R)-2-tert-butoxycarbonylamino-2-cyano-cyclopropylmethyl ester 在 potassium carbonate 、 caesium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.75h， 生成 (1R,2R)-(+)-1--2-(mercaptomethyl)cyclopropane-1-carbonitrile
  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：

  (1R,5R)-(-)-1-(tert-butoxycarbonyl)-2-oxo-3-oxabicyclo<3.1.0>hexane 在 吡啶 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 叠氮磷酸二苯酯 、 三乙胺 、 对甲苯磺酰氯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 74.08h， 生成 Methanesulfonic acid (1R,2R)-2-tert-butoxycarbonylamino-2-cyano-cyclopropylmethyl ester
  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

文献信息

• Asymmetric syntheses of all four stereoisomers of 2,3-methanomethionine
  作者：Kevin Burgess、Kwok Kan Ho

  DOI：10.1021/jo00048a028

  日期：1992.10

  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.