4-O-[(4-methoxyphenyl)methyl] 1-O-prop-2-enyl (2S)-2-(prop-2-enoxycarbonylamino)butanedioate | 180712-39-4

• 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: 4-O-[(4-methoxyphenyl)methyl] 1-O-prop-2-enyl (2S)-2-(prop-2-enoxycarbonylamino)butanedioate
• CAS: 180712-39-4
• 化学式: C₁₉H₂₃NO₇
• 分子量: 377.394
• InChiKey: RVVRIQLCFLGNLL-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-O-[(4-methoxyphenyl)methyl] 1-O-prop-2-enyl (2S)-2-(prop-2-enoxycarbonylamino)butanedioate 在 四氢吡咯 、 四(三苯基膦)钯 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 反应 27.75h， 生成 (+)-2R-S-(2,4-dimethoxybenzyl)-β-(4-methoxybenzyl)-3-mercaptoaspartyl-D-valine-(4-methoxybenzyl) ester
  参考文献：
  名称：

  Electrophilic sulfenylation in a stereocontrolled synthesis of protected (2R,3R)-3-mercaptoaspartic acid from -aspartic acid

  摘要：

  A novel electrophilic sulfenylating agent, (2,4-dimethoxybenzylthio)-4-methylphenyl sulfonate (13) was developed to give thiols bearing an acid labile protecting group. This was subsequently used to prepare in a stereocontrolled manner, a protected form of (2R,3R)-3-mercaptoaspartic acid which was incorporated into a tripeptide. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0040-4020(96)00765-x
• 作为产物：
  描述：

  Alloc-L-Asp-OH 在 4-二甲氨基吡啶 、 乙酸酐 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 125.0h， 生成 4-O-[(4-methoxyphenyl)methyl] 1-O-prop-2-enyl (2S)-2-(prop-2-enoxycarbonylamino)butanedioate
  参考文献：
  名称：

  Electrophilic sulfenylation in a stereocontrolled synthesis of protected (2R,3R)-3-mercaptoaspartic acid from -aspartic acid

  摘要：

  A novel electrophilic sulfenylating agent, (2,4-dimethoxybenzylthio)-4-methylphenyl sulfonate (13) was developed to give thiols bearing an acid labile protecting group. This was subsequently used to prepare in a stereocontrolled manner, a protected form of (2R,3R)-3-mercaptoaspartic acid which was incorporated into a tripeptide. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0040-4020(96)00765-x

文献信息

• Electrophilic sulfenylation in a stereocontrolled synthesis of protected (2R,3R)-3-mercaptoaspartic acid from -aspartic acid
  作者：Norio Shibata、Jack E. Baldwin、Adam Jacobs、Mark E. Wood

  DOI：10.1016/0040-4020(96)00765-x

  日期：1996.9

  A novel electrophilic sulfenylating agent, (2,4-dimethoxybenzylthio)-4-methylphenyl sulfonate (13) was developed to give thiols bearing an acid labile protecting group. This was subsequently used to prepare in a stereocontrolled manner, a protected form of (2R,3R)-3-mercaptoaspartic acid which was incorporated into a tripeptide. Copyright (C) 1996 Published by Elsevier Science Ltd