tert-butyl (1S,2R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(methylsulfonyloxymethyl)cyclopropane-1-carboxylate | 154704-03-7

• 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: tert-butyl (1S,2R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(methylsulfonyloxymethyl)cyclopropane-1-carboxylate
• CAS: 154704-03-7
• 化学式: C₁₅H₂₇NO₇S
• 分子量: 365.448
• InChiKey: IAXCMYYTTWUKJT-BONVTDFDSA-N

物化性质

• 沸点：
  483.8±28.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,2R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(methylsulfonyloxymethyl)cyclopropane-1-carboxylate 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 tert-butyl (1S,2S)-2-(aminomethyl)-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylate
  参考文献：
  名称：

  Asymmetric Syntheses of Protected Derivatives of Carnosadine and Its Stereoisomers as Conformationally Constrained Surrogates for Arginine

  摘要：

  All four stereoisomers of carnosadine were shown to be accessible from the lactone 1 or the diester 10 (or their enantiomers). Members of the cis series (Z-cyclo-Arg') were obtained via a sequence involving opening lactone 1 with ammonia, Hofmann rearrangement, and incorporation of the guanidine group via an azide (3). The trans series (i.e. The E-cyclo-Arg' series) was prepared via a route which is similar, except that it begins with hydrolysis of the less hindered ester functionality of diester 10. Products from both series were manipulated into protected forms for peptide synthesis using the BOC or the FMOC approach.

  DOI：

  10.1021/jo00087a039
• 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 为溶剂， 反应 18.08h， 生成 tert-butyl (1S,2R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(methylsulfonyloxymethyl)cyclopropane-1-carboxylate
  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 the stereoisomers of protected 2,3-methanoglutamine
  作者：Kevin Burgess、Dong Yeol Lim

  DOI：10.1016/0040-4039(95)01659-6

  日期：1995.10

  Chirons 1 and 2, both from mannitol, were used to prepare enantiomerically pure cis and trans stereoisomers of 2,3-methanoglutamine (cyclo-Gln) in a protected form suitable for solid phase peptide synthesis.

  Chirons 1和2，无论是从甘露糖醇，用于制备对映体纯的顺式和反式2,3- methanoglutamine（立体异构体环-谷氨酰胺以适合于固相肽合成被保护的形式）。
• 1-Aminocylopropane-1-carboxylic acid derivatives as ligands at the glycine-binding site of the N-methyl-D-aspartate receptor
  作者：Cesarino Balsamini、Annalida Bedini、Gilberto Spadoni、Giorgio Tarzia、Andrea Tontini、Walter Balduini、Mauro Cimino

  DOI：10.1016/s0014-827x(98)00005-6

  日期：1998.3

  Several 1-aminocyclopropane-1-carboxylic acid derivatives were prepared and tested for activity at the glycine-binding site of the N-methyl-D-aspartate (NMDA) receptor complex. Structural modifications involved the amino group, the carboxylic function or position 2 of the ring. When tested in a [H-3]-MK-801 binding assay in the presence of glutamic acid, some of the compounds were able to activate the receptor. Two of them (3e and 6) are selective ligands for the glycine site of the NMDA receptor. (C) 1998 Elsevier Science S.A. All rights reserved.
• 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.
• Asymmetric Syntheses of Protected Derivatives of Carnosadine and Its Stereoisomers as Conformationally Constrained Surrogates for Arginine
  作者：Kevin Burgess、Dongyeol Lim、Kwok-Kan Ho、Chun-Yen Ke

  DOI：10.1021/jo00087a039

  日期：1994.4

  All four stereoisomers of carnosadine were shown to be accessible from the lactone 1 or the diester 10 (or their enantiomers). Members of the cis series (Z-cyclo-Arg') were obtained via a sequence involving opening lactone 1 with ammonia, Hofmann rearrangement, and incorporation of the guanidine group via an azide (3). The trans series (i.e. The E-cyclo-Arg' series) was prepared via a route which is similar, except that it begins with hydrolysis of the less hindered ester functionality of diester 10. Products from both series were manipulated into protected forms for peptide synthesis using the BOC or the FMOC approach.