(S)-2-Benzyloxycarbonylamino-5-[(R)-1-((1R,2S)-1-benzyloxycarbonyl-2-methoxy-propylcarbamoyl)-2-benzylsulfanyl-ethylcarbamoyl]-pentanoic acid benzyl ester | 209050-98-6

• 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-Benzyloxycarbonylamino-5-[(R)-1-((1R,2S)-1-benzyloxycarbonyl-2-methoxy-propylcarbamoyl)-2-benzylsulfanyl-ethylcarbamoyl]-pentanoic acid benzyl ester
• 英文别名: benzyl (2S)-6-[[(2R)-3-benzylsulfanyl-1-[[(2R,3S)-3-methoxy-1-oxo-1-phenylmethoxybutan-2-yl]amino]-1-oxopropan-2-yl]amino]-6-oxo-2-(phenylmethoxycarbonylamino)hexanoate
• CAS: 209050-98-6
• 化学式: C₄₃H₄₉N₃O₉S
• 分子量: 783.943
• InChiKey: LGTLQNOTPISHIA-PWTSDHCZSA-N

物化性质

• 沸点：
  959.980±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.229±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  56.0
• 可旋转键数：
  22.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  158.36
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Benzyloxycarbonylamino-5-[(R)-1-((1R,2S)-1-benzyloxycarbonyl-2-methoxy-propylcarbamoyl)-2-benzylsulfanyl-ethylcarbamoyl]-pentanoic acid benzyl ester 在 氨 、 氧气 、 sodium 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (S)-2-Amino-5-[(R)-2-[(R)-2-((S)-5-amino-5-carboxy-pentanoylamino)-2-((1R,2S)-1-carboxy-2-methoxy-propylcarbamoyl)-ethyldisulfanyl]-1-((1R,2S)-1-carboxy-2-methoxy-propylcarbamoyl)-ethylcarbamoyl]-pentanoic acid
  参考文献：
  名称：

  Synthesis of δ-(l-α-aminoadipoyl)-l-cysteinyl-d-(O-methyl)-d-allothreonine a substrate for isopenicillin-N synthase and its O-methyl-d-threonine epimer

  摘要：

  The paper describes the synthesis of two epimeric tripeptides delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-threonine (13) and 6-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-allothreonine (14), modified substrates for the isopenicillin-N synthase enzyme. The D-allothreonine tripeptide (14)has been shown to be an excellent substrate for the enzyme whereas the D-threonine epimer did not react at all. The compound formed by the enzyme with the D-allothreonine tripeptide is a new 2-alpha-methoxypenicillin. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00280-4
• 作为产物：
  描述：

  (2R,3R)-2-Benzyloxycarbonylamino-3-methoxy-butyric acid benzyl ester 在 氢溴酸 、 溶剂黄146 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (S)-2-Benzyloxycarbonylamino-5-[(R)-1-((1R,2S)-1-benzyloxycarbonyl-2-methoxy-propylcarbamoyl)-2-benzylsulfanyl-ethylcarbamoyl]-pentanoic acid benzyl ester
  参考文献：
  名称：

  Synthesis of δ-(l-α-aminoadipoyl)-l-cysteinyl-d-(O-methyl)-d-allothreonine a substrate for isopenicillin-N synthase and its O-methyl-d-threonine epimer

  摘要：

  The paper describes the synthesis of two epimeric tripeptides delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-threonine (13) and 6-(L-alpha-aminoadipoyl)-L-cysteinyl-D-(O-methyl)-D-allothreonine (14), modified substrates for the isopenicillin-N synthase enzyme. The D-allothreonine tripeptide (14)has been shown to be an excellent substrate for the enzyme whereas the D-threonine epimer did not react at all. The compound formed by the enzyme with the D-allothreonine tripeptide is a new 2-alpha-methoxypenicillin. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00280-4