(S)-2-{(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid methyl ester | 201408-94-8

• 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: (S)-2-{(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid methyl ester
• CAS: 201408-94-8
• 化学式: C₂₉H₃₆N₄O₇S
• 分子量: 584.693
• InChiKey: XQBYEQPHIYOEBB-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  136.9
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-2-{(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid methyl ester 在 二甲基硫 、 Amberlite 410 anion exchange resin (OH^- form) 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 8.0h， 生成 (S)-2-[(S)-3-(1H-Imidazol-4-yl)-2-methylamino-propionylamino]-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  The effects of N-methylation on the enantioselectivity of catalysis by cyclo[(R)-His-(R)-Phe]

  摘要：

  The cyclic dipeptide cyclo[(R)-His-(R)-Phe] 1 has been known since 1981 to catalyze the enantioselective formation of cyanohydrins from aldehydes and HCN. Although 1 has proved to be very effective in the production of optically active cyanohydrins, the precise structure of its catalytically active form remains unresolved. Two derivatives, in which the two amides in 1 were independently N-methylated, were synthesized as probes of the structural and functional requirements for catalysis by 1. Both derivatives were far more soluble in organic solvents and were found to catalyze the formation of racemic cyanohydrin, but differed greatly in their turnover rates. Mixtures of the two derivatives with each other and with 1 were also examined as hydrocyanation catalysts. Only the mixtures containing 1 demonstrated any enantioselectivity, but did not appear any more competent as catalysts than reduced quantities of 1. From these data, it is concluded that both amide bonds are essential for effective catalysis by 1, but that the amide containing the His N-alpha appears to be involved in interactions with the substrate while the other amide plays a structural role, possibly for self-associative hydrogen bonding. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00573-9
• 作为产物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 、 N^α-(tert-butyloxycarbonyl)-N^α-methyl-N^im-tosyl-L-histidine 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.3h， 以73%的产率得到(S)-2-{(S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-propionylamino}-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  The effects of N-methylation on the enantioselectivity of catalysis by cyclo[(R)-His-(R)-Phe]

  摘要：

  The cyclic dipeptide cyclo[(R)-His-(R)-Phe] 1 has been known since 1981 to catalyze the enantioselective formation of cyanohydrins from aldehydes and HCN. Although 1 has proved to be very effective in the production of optically active cyanohydrins, the precise structure of its catalytically active form remains unresolved. Two derivatives, in which the two amides in 1 were independently N-methylated, were synthesized as probes of the structural and functional requirements for catalysis by 1. Both derivatives were far more soluble in organic solvents and were found to catalyze the formation of racemic cyanohydrin, but differed greatly in their turnover rates. Mixtures of the two derivatives with each other and with 1 were also examined as hydrocyanation catalysts. Only the mixtures containing 1 demonstrated any enantioselectivity, but did not appear any more competent as catalysts than reduced quantities of 1. From these data, it is concluded that both amide bonds are essential for effective catalysis by 1, but that the amide containing the His N-alpha appears to be involved in interactions with the substrate while the other amide plays a structural role, possibly for self-associative hydrogen bonding. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00573-9