N-Cbz-(O-Me)-E-2,3-L-dehydroglutamate OBO ester | 335170-37-1

• 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: N-Cbz-(O-Me)-E-2,3-L-dehydroglutamate OBO ester
• 英文别名: methyl (E,4S)-4-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-4-(phenylmethoxycarbonylamino)but-2-enoate
• CAS: 335170-37-1
• 化学式: C₁₉H₂₃NO₇
• 分子量: 377.394
• InChiKey: AZWYBLYJERNUQU-KGJMHHKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-Cbz-(O-Me)-E-2,3-L-dehydroglutamate OBO ester 在 盐酸 作用下， 生成 (E)-(S)-4-Amino-pent-2-enedioic acid 1-methyl ester
  参考文献：
  名称：

  Synthesis of enantiomerically enriched β,γ-unsaturated-α-amino acids

  摘要：

  A variety of enantiomerically enriched beta,gamma -unsaturated-alpha -amino acids are synthesized by olefination of a Cbz-protected serine aldehyde equivalent, readily prepared from serine. A cyclic ortho ester protecting group is employed to minimize racemization. The deprotected amino acids are obtained in good yield, ranging from 70-95% ee, with double-bond geometry determined by the type of Wittig reagent used. Isotopically labeled side chains are readily introduced by this procedure, and free gamma-C-13-vinylglycine was prepared in 44% yield from the protected serine aldehyde synthon. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01146-7
• 作为产物：
  描述：

  3-甲基-3-羟甲基氧杂环丁烷 在 草酰氯 、 三氟化硼乙醚 、 二甲基亚砜 、 sodium iodide 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 57.83h， 生成 N-Cbz-(O-Me)-E-2,3-L-dehydroglutamate OBO ester
  参考文献：
  名称：

  Synthesis of enantiomerically enriched β,γ-unsaturated-α-amino acids

  摘要：

  A variety of enantiomerically enriched beta,gamma -unsaturated-alpha -amino acids are synthesized by olefination of a Cbz-protected serine aldehyde equivalent, readily prepared from serine. A cyclic ortho ester protecting group is employed to minimize racemization. The deprotected amino acids are obtained in good yield, ranging from 70-95% ee, with double-bond geometry determined by the type of Wittig reagent used. Isotopically labeled side chains are readily introduced by this procedure, and free gamma-C-13-vinylglycine was prepared in 44% yield from the protected serine aldehyde synthon. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01146-7

文献信息

• Synthesis of Syn and Anti Isomers of <i>trans</i>-Cyclopropyl Arginine
  作者：Dan Fishlock、J. Guy Guillemette、Gilles A. Lajoie

  DOI：10.1021/jo016242e

  日期：2002.4.1

  starting from the alpha-OBO-protected Cbz-dehydroglutamate. Cyclopropanation is effected by diazomethane addition followed by irradiation of the resulting pyrazoline and gives a 3:1 mixture of syn:anti isomers that can be separated by crystallization. Reduction of the ester to the alcohol followed by guanylation gives the fully protected cyclopropyl arginine analogues. The CBZ protecting groups are

  在一氧化氮合酶（NOS）底物和抑制剂的背景下，目前对精氨酸及其结构类似物有相当大的兴趣。特别受关注的是构象受限的精氨酸类似物，用于探测三种NOS同工型的活性位点。描述了一种简单的方法，该方法从α-OBO保护的Cbz-脱氢谷氨酸开始制备顺式和反式环丙基精氨酸。加入重氮甲烷，然后辐射所得吡唑啉，进行环丙烷化反应，生成3：1的syn：anti异构体混合物，可通过结晶分离。将酯还原成醇，然后进行鸟苷酸化，得到完全保护的环丙基精氨酸类似物。
• Stereoselective Synthesis of <scp>l</scp>-2-(Carboxycyclopropyl)glycines via Stereocontrolled 1,3-Dipolar Cycloadditions of Diazomethane on <i>Z</i>- and <i>E</i>-3,4-<scp>l</scp>-Didehydroglutamates OBO Esters
  作者：Joan Rifé、Rosa M. Ortuño、Gilles A. Lajoie

  DOI：10.1021/jo991066j

  日期：1999.11.1