苄基N-[(苄氧基)羰基]组氨酸酯 | 20794-07-4

• 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
• 中文名称: 苄基N-[(苄氧基)羰基]组氨酸酯
• 英文名称: N^α-(carbobenzyloxy)histidine benzyl ester
• 英文别名: N^α-Benzyloxycarbonyl-L-histidinbenzylester；Cbz-L-His-OBn；N^α-benzyloxycarbonyl-histidine benzyl ester；benzyl (2S)-3-(1H-imidazol-5-yl)-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 20794-07-4
• 化学式: C₂₁H₂₁N₃O₄
• 分子量: 379.415
• InChiKey: NSUWDHSSVSZBJZ-IBGZPJMESA-N

物化性质

• 沸点：
  640.9±55.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  93.3
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• WGK Germany：
  3
• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  苄基N-[(苄氧基)羰基]组氨酸酯 、 1,5-环己二烯-1-羧酸,3,4-二羰基-5-(苯基甲氧基)-,苯基甲基酯 以 四氢呋喃 为溶剂， 反应 20.0h， 以16%的产率得到benzyl 3,4-dihydroxy-2-[4-[(2S)-3-oxo-3-phenylmethoxy-2-(phenylmethoxycarbonylamino)propyl]imidazol-1-yl]-5-phenylmethoxybenzoate
  参考文献：
  名称：

  Galloyl-Derived Orthoquinones as Reactive Partners in Nucleophilic Additions and Diels−Alder Dimerizations:  A Novel Route to the Dehydrodigalloyl Linker Unit of Agrimoniin-Type Ellagitannins

  摘要：

  Orthochloranil-mediated oxidation of galloyl monoethers furnishes the derived orthoquinones in excellent yield. These reactive electrophiles participate in a variety of nucleophilic addition reactions with heteroatomic and carbanionic partners. In addition, Lewis acid-mediated dimerization of the orthoquinones provides an efficient route to dehydrodigalloyl-type diaryl ether units characteristic of several ellagitannin natural products. The implications for ellagitannin biosynthesis and gallotannin-protein covalent attachment are discussed.

  DOI：

  10.1021/jo961043u
• 作为产物：
  描述：

  苯甲醇 、 N-Cbz-L-组氨酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到苄基N-[(苄氧基)羰基]组氨酸酯
  参考文献：
  名称：

  Galloyl-Derived Orthoquinones as Reactive Partners in Nucleophilic Additions and Diels−Alder Dimerizations:  A Novel Route to the Dehydrodigalloyl Linker Unit of Agrimoniin-Type Ellagitannins

  摘要：

  Orthochloranil-mediated oxidation of galloyl monoethers furnishes the derived orthoquinones in excellent yield. These reactive electrophiles participate in a variety of nucleophilic addition reactions with heteroatomic and carbanionic partners. In addition, Lewis acid-mediated dimerization of the orthoquinones provides an efficient route to dehydrodigalloyl-type diaryl ether units characteristic of several ellagitannin natural products. The implications for ellagitannin biosynthesis and gallotannin-protein covalent attachment are discussed.

  DOI：

  10.1021/jo961043u

文献信息

• Peptide Synthesis in Aqueous Solution. V. Properties and Reactivities of (<i>p</i>-Hydroxyphenyl)benzylmethylsulfonium Salts for Direct Benzyl Esterification of<i>N</i>-Acylpeptides
  作者：Takashi Nakata、Masaru Nakatani、Masatoshi Takahashi、Jiro Okai、Yoshiaki Kawaoka、Katsushige Kouge、Hideo Okai

  DOI：10.1246/bcsj.69.1099

  日期：1996.4

  Some (p-hydroxyphenyl)benzylmethylsulfonium salts were prepared. These compounds generated a benzyl cation and converted not only N-acylamino acids but also N-acylpeptides into their corresponding benzyl esters without causing the racemization.

  制备了一些（对羟基苯基）苄基甲基硫盐。这些化合物生成了苄基阳离子，并且不仅将N-酰基氨基酸，还将N-酰基肽转化为其相应的苄基酯，而没有引起消旋化。
• Synthesis of Histidinoalanine: A Comparison of β-Lactone and Sulfamidate Electrophiles
  作者：Carol M. Taylor、Samanthi Thabrew De Silva

  DOI：10.1021/jo200744d

  日期：2011.7.15

  Previous syntheses of histidinoalanine (HAL) have led to mixtures of regioisomers and/or stereoisomers. For example, opening of N-Cbz-D-serine-beta-lactone (6) with Boc-L-His-OMe (5) gave a 2:1 mixture of tau- and pi-regioisomers. The sulfamidate 10, derived from N-benzyl-D-serine methyl ester (11), was reacted with Boc-L-His-OMe (5) to give the tau-HAL derivative 17 as a single isomer in 57% yield. A similarly prepared tau-HAL 19, bearing protecting groups that were all hydrogenolytically labile, led to the free bis-amino acid, tau-L-histidinyl-D-alanine (tau-4), as a salt-free standard for amino acid analysis.
• Galloyl-Derived Orthoquinones as Reactive Partners in Nucleophilic Additions and Diels−Alder Dimerizations:  A Novel Route to the Dehydrodigalloyl Linker Unit of Agrimoniin-Type Ellagitannins
  作者：Ken S. Feldman、Stéphane Quideau、Heidi M. Appel

  DOI：10.1021/jo961043u

  日期：1996.1.1

  Orthochloranil-mediated oxidation of galloyl monoethers furnishes the derived orthoquinones in excellent yield. These reactive electrophiles participate in a variety of nucleophilic addition reactions with heteroatomic and carbanionic partners. In addition, Lewis acid-mediated dimerization of the orthoquinones provides an efficient route to dehydrodigalloyl-type diaryl ether units characteristic of several ellagitannin natural products. The implications for ellagitannin biosynthesis and gallotannin-protein covalent attachment are discussed.