N-(9-fluorenylmethoxycarbonyl)-D-valine-(4-methoxybenzyl) ester | 182952-86-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9-fluorenylmethoxycarbonyl)-D-valine-(4-methoxybenzyl) ester
• 英文别名: (4-methoxyphenyl)methyl (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutanoate
• CAS: 182952-86-9
• 化学式: C₂₈H₂₉NO₅
• 分子量: 459.542
• InChiKey: MXMOPUYZYQMXLC-AREMUKBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-D-valine-(4-methoxybenzyl) ester 在 1-羟基苯并三唑 、 二乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2R,3R)-3-Allyloxycarbonylamino-2-(2,4-dimethoxy-benzylsulfanyl)-N-[(R)-1-(4-methoxy-benzyloxycarbonyl)-2-methyl-propyl]-succinamic acid 4-methoxy-benzyl 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：

  4-甲氧基苄醇 、 Fmoc-D-缬氨酸 在 吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以44%的产率得到N-(9-fluorenylmethoxycarbonyl)-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

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