(+)-(1S,2R)-2-(benzyloxymethyl)-1-(ethoxycarbonyl)cyclopropane-1-carboxylic acid | 154704-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-(1S,2R)-2-(benzyloxymethyl)-1-(ethoxycarbonyl)cyclopropane-1-carboxylic acid
• 英文别名: (1S,2R)-1-ethoxycarbonyl-2-(phenylmethoxymethyl)cyclopropane-1-carboxylic acid
• CAS: 154704-20-8
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: WSPWDKYMPKJCSK-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-(1S,2R)-2-(benzyloxymethyl)-1-(ethoxycarbonyl)cyclopropane-1-carboxylic acid 在 palladium on activated charcoal sodium hydroxide 、 sodium azide 、 叠氮磷酸二苯酯 、 氨 、 氢气 、 silver nitrate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 137.5h， 生成 (1R,2S)-1--2-<<(2-toluenesulfonyl)guanidino>methyl>cyclopropane-1-carboxylic acid
  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：

  (S)-4-(Benzyloxymethyl)-2,2-dioxo-1,3,2-dioxathiolane 在 sodium hydride 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 68.33h， 生成 (+)-(1S,2R)-2-(benzyloxymethyl)-1-(ethoxycarbonyl)cyclopropane-1-carboxylic acid
  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

文献信息

• Large Scale Syntheses of N-Protected 2,3-Methanomethionine Stereoisomers
  作者：Kevin Burgess、Chun-Yen Ke

  DOI：10.1055/s-1996-4425

  日期：1996.12

  Three stereoisomers of N-protected forms of 2,3-methanomethionine (cyclopropyl derivatives of methionine, or ”cyclo-Met”) were prepared. Two of the syntheses developed involved diol (S)-1, which was more easily obtained from L-gulono-1,4-lactone than via juxtaposition of the benzyl protection of (R)-1. The cis-cyclo-Met derivative (cis refers to the orientation of the side chain relative to the amino functionality), FMOC-(2R,3S)-cyclo-Met, was obtained via a route based on a previous synthesis of (2R,3S)-cyclo-Met from the lactone 3, but the protected trans-cyclo-Met, BOC-(2R,3S)-cyclo-Met, was obtained via an improved procedure that does not involve lactone 3.

  我们制备了三种 2,3-甲硫氨酸 N 保护形式的立体异构体（甲硫氨酸的环丙基衍生物，或称 "环甲硫氨酸"）。其中两种合成涉及二元醇 (S)-1，它更容易从 L-古洛萘-1,4-内酯中获得，而不是通过并置苄基保护的 (R)-1。顺式环-Met 衍生物（顺式指侧链相对于氨基官能团的取向）FMOC-(2R,3S)-环-Met 是通过以前从内酯 3 合成 (2R,3S)-cyclo-Met 的路线获得的，但受保护的反式环-Met BOC-(2R,3S)-cyclo-Met 则是通过一种不涉及内酯 3 的改进程序获得的。
• SUBSTITUTED SPIROPYRIDO[1,2-a]PYRAZINE DERIVATIVE AND MEDICINAL USE THEREOF AS HIV INTEGRASE INHIBITOR
  申请人：JAPAN TOBACCO INC.

  公开号：US20170044156A1

  公开（公告）日：2017-02-16

  Provided is a substituted spiropyrido[1,2-a]pyrazine derivative or a pharmaceutically acceptable salt thereof, which is useful as an anti-HIV agent. The present invention relates to a compound represented by the following formula [I] or [II] or a pharmaceutically acceptable salt thereof: wherein each symbol is as defined in the specification.
• 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.