(E)-(S)-2-tert-Butoxycarbonylamino-6-hydroxy-hex-4-enoic acid methyl ester | 110579-52-7

• 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: (E)-(S)-2-tert-Butoxycarbonylamino-6-hydroxy-hex-4-enoic acid methyl ester
• 英文别名: methyl (E,2S)-6-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]hex-4-enoate
• CAS: 110579-52-7
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: CVSFNTQNWJKOOA-CYNONHLPSA-N

物化性质

• 沸点：
  381.8±42.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(S)-2-tert-Butoxycarbonylamino-6-hydroxy-hex-4-enoic acid methyl ester 在 bis[1,2-bis(diphenylphosphino)ethane]palladium(0) 吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 methyl (E,2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-[(2-methylpropan-2-yl)oxycarbonyl-[(2-methylpropan-2-yl)oxycarbonyloxy]amino]hex-4-enoate
  参考文献：
  名称：

  Palladium (0) catalyzed amination with N,O-bis-ter-Boc hydroxylamine. Synthesis of (+)-N6-hydroxylysine

  摘要：

  Palladium-catalyzed reaction of allyl esters with (N,O)-bis-ter-Boc hydroxylamine 2 gives protected N-allylhydroxylamines. A synthetic application to (+)-N6-hydroxylysine component of mycobactin T is also described.

  DOI：

  10.1016/s0040-4039(00)77516-2
• 作为产物：
  描述：

  methyl (E,2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxohex-4-enoate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以87%的产率得到(E)-(S)-2-tert-Butoxycarbonylamino-6-hydroxy-hex-4-enoic acid methyl ester
  参考文献：
  名称：

  A facile synthesis of (S)-gizzerosine, a potent agonist of the histamine H2-receptor

  摘要：

  A simple and direct approach for the synthesis of (S)-gizzerosine, an amino acid responsible for the disease, black vomit, and a potent histamine H-2-receptor, has been developed in 10 steps and in 31% overall yield from L-aspartic acid. The key steps involved a two-carbon homologation of an L-aspartic acid semi-aldehyde and direct alkylation of unprotected histamine with a 6-hydroxynorleucine derivative. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.165

文献信息

• An efficient route to 1,3-amino hydroxyl system via electrophilic lactonization of 2-amino-4-pentenoic acid derivatives. Stereoselective synthesis of (−)-bulgecinine
  作者：Yasufumi Ohfune、Keiko Hori、Masahiro Sakaitani

  DOI：10.1016/s0040-4039(00)85403-9

  日期：1986.1

  Several γ-hydroxy-α-amino acid systems were prepared stereoselectively from 2-amino-4-pentenoic acid derivatives using electrophilic lactonization. This strategy was applied to the synthesis of a highly functionalized proline analogue, (−)-bulgecinine (4).

  使用亲电子内酯化作用，由2-氨基-4-戊烯酸衍生物立体选择性地制备了几种γ-羟基-α-氨基酸系统。该策略被用于合成高度功能化的脯氨酸类似物（-）-bulgecinine（4）。
• Palladium (0) catalyzed amination with N,O-bis-ter-Boc hydroxylamine. Synthesis of (+)-N6-hydroxylysine
  作者：Jean-Pierre Genet、Serge Thorimbert、Anne-Marie Touzin

  DOI：10.1016/s0040-4039(00)77516-2

  日期：1993.2

  Palladium-catalyzed reaction of allyl esters with (N,O)-bis-ter-Boc hydroxylamine 2 gives protected N-allylhydroxylamines. A synthetic application to (+)-N6-hydroxylysine component of mycobactin T is also described.
• A facile synthesis of (S)-gizzerosine, a potent agonist of the histamine H2-receptor
  作者：Kate N. Fanning、Andrew Sutherland

  DOI：10.1016/j.tetlet.2007.09.165

  日期：2007.11

  A simple and direct approach for the synthesis of (S)-gizzerosine, an amino acid responsible for the disease, black vomit, and a potent histamine H-2-receptor, has been developed in 10 steps and in 31% overall yield from L-aspartic acid. The key steps involved a two-carbon homologation of an L-aspartic acid semi-aldehyde and direct alkylation of unprotected histamine with a 6-hydroxynorleucine derivative. (c) 2007 Elsevier Ltd. All rights reserved.