dibenzyl Nα-tert-carbobenzyloxy-Nα'-benzyl-τ-L-histidino-D-alaninate | 1311981-49-3

• 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: dibenzyl Nα-tert-carbobenzyloxy-Nα'-benzyl-τ-L-histidino-D-alaninate
• 英文别名: benzyl (2S)-3-[1-[(2R)-2-(benzylamino)-3-oxo-3-phenylmethoxypropyl]imidazol-4-yl]-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 1311981-49-3
• 化学式: C₃₈H₃₈N₄O₆
• 分子量: 646.743
• InChiKey: GNTREYUQVAJRBU-OIDHKYIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  48
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dibenzyl Nα-tert-carbobenzyloxy-Nα'-benzyl-τ-L-histidino-D-alaninate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 48.0h， 以88%的产率得到τ-L-histidino-D-alanine
  参考文献：
  名称：

  Synthesis of Histidinoalanine: A Comparison of β-Lactone and Sulfamidate Electrophiles

  摘要：

  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.

  DOI：

  10.1021/jo200744d
• 作为产物：
  描述：

  N-benzyl-D-serine benzyl ester 在 吡啶 、 sodium periodate 、 氯化亚砜 、 ruthenium(III) chloride trihydrate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 7.92h， 生成 dibenzyl Nα-tert-carbobenzyloxy-Nα'-benzyl-τ-L-histidino-D-alaninate
  参考文献：
  名称：

  Synthesis of Histidinoalanine: A Comparison of β-Lactone and Sulfamidate Electrophiles

  摘要：

  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.

  DOI：

  10.1021/jo200744d

文献信息

• 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.