3-Bromo-N-[(phenylmethoxy)carbonyl]-D-alanine methyl ester | 200344-41-8

• 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: 3-Bromo-N-[(phenylmethoxy)carbonyl]-D-alanine methyl ester
• 英文别名: methyl (2S)-3-bromo-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 200344-41-8
• 化学式: C₁₂H₁₄BrNO₄
• 分子量: 316.151
• InChiKey: PIONCLUETHSRCR-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Bromo-N-[(phenylmethoxy)carbonyl]-D-alanine methyl ester 、 N-叔丁基氧羰基-L-组氨酸甲酯 在 magnesium triflate 、 4-二甲氨基吡啶 作用下， 以 丙酮 为溶剂， 反应 13.0h， 以44%的产率得到dimethyl Nα-tert-butoxycarbonyl-Nα'-carbobenzyloxy-τ-L-histidino-D-alaninate
  参考文献：
  名称：

  Lewis acid facilitated regioselective synthesis of τ-histidinoalanine

  摘要：

  tau-Histidinoalanine, with an unusual cross-link between His and Ala, is the central component of theonellamides, a family of bioactive peptidic natural products. Previous syntheses of this residue were plagued with low regioselectivity in the alkylation step. Herein, we report two novel routes to tau-histidinoalanine, involving alkylation of Boc-His-OMe with a serine-derived beta-lactone and beta-bromoalanine, respectively, as the electrophiles. The use of Mg(OTf)(2) as a catalyst was found to be essential to ensure high regioselectivity for the tau-isomer, presumably due to the formation of a six-membered ring chelation involving the pi-nitrogen atom of histidine. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.008
• 作为产物：
  描述：

  N-Z-D-丝氨酸甲酯 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 3-Bromo-N-[(phenylmethoxy)carbonyl]-D-alanine methyl ester
  参考文献：
  名称：

  Lewis acid facilitated regioselective synthesis of τ-histidinoalanine

  摘要：

  tau-Histidinoalanine, with an unusual cross-link between His and Ala, is the central component of theonellamides, a family of bioactive peptidic natural products. Previous syntheses of this residue were plagued with low regioselectivity in the alkylation step. Herein, we report two novel routes to tau-histidinoalanine, involving alkylation of Boc-His-OMe with a serine-derived beta-lactone and beta-bromoalanine, respectively, as the electrophiles. The use of Mg(OTf)(2) as a catalyst was found to be essential to ensure high regioselectivity for the tau-isomer, presumably due to the formation of a six-membered ring chelation involving the pi-nitrogen atom of histidine. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.008

文献信息

• Lewis acid facilitated regioselective synthesis of τ-histidinoalanine
  作者：Ju Wu、Bing Ma、Yuehui Wang、Yue Zhang、Shenghu Yan、Steven L. Castle

  DOI：10.1016/j.tetlet.2014.04.008

  日期：2014.5

  tau-Histidinoalanine, with an unusual cross-link between His and Ala, is the central component of theonellamides, a family of bioactive peptidic natural products. Previous syntheses of this residue were plagued with low regioselectivity in the alkylation step. Herein, we report two novel routes to tau-histidinoalanine, involving alkylation of Boc-His-OMe with a serine-derived beta-lactone and beta-bromoalanine, respectively, as the electrophiles. The use of Mg(OTf)(2) as a catalyst was found to be essential to ensure high regioselectivity for the tau-isomer, presumably due to the formation of a six-membered ring chelation involving the pi-nitrogen atom of histidine. (C) 2014 Elsevier Ltd. All rights reserved.