(S)-1-{(R)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentanoylamino]-3-methanesulfinyl-propionyl}-pyrrolidine-2-carboxylic acid methyl ester | 207273-97-0

• 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)-1-{(R)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentanoylamino]-3-methanesulfinyl-propionyl}-pyrrolidine-2-carboxylic acid methyl ester
• 英文别名: methyl (2S)-1-[(2R)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylpentanoyl]amino]-3-methylsulfinylpropanoyl]pyrrolidine-2-carboxylate
• CAS: 207273-97-0
• 化学式: C₃₁H₃₉N₃O₇S
• 分子量: 597.733
• InChiKey: OSTNXFWTKHXBET-GXZUTTDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  150
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-1-{(R)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentanoylamino]-3-methanesulfinyl-propionyl}-pyrrolidine-2-carboxylic acid methyl ester 以 1,4-二氧六环 为溶剂， 反应 15.0h， 以84%的产率得到(S)-1-{2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentanoylamino]-acryloyl}-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  A highly efficient route to dehydroalanine containing peptides

  摘要：

  A routine method for the synthesis of dehydroalanine containing peptides has been developed. These residues are introduced as S-methyl cysteines which are subsequently oxidised and eliminated. The approach is compatible with both Boc and Fmoc protection strategies and can allow the introduction of a number of alpha beta unsaturated amino acids into peptides during synthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00258-5
• 作为产物：
  描述：

  L-脯氨酸甲酯 在 sodium periodate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 (S)-1-{(R)-2-[(S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-4-methyl-pentanoylamino]-3-methanesulfinyl-propionyl}-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  A highly efficient route to dehydroalanine containing peptides

  摘要：

  A routine method for the synthesis of dehydroalanine containing peptides has been developed. These residues are introduced as S-methyl cysteines which are subsequently oxidised and eliminated. The approach is compatible with both Boc and Fmoc protection strategies and can allow the introduction of a number of alpha beta unsaturated amino acids into peptides during synthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00258-5

文献信息

• A highly efficient route to dehydroalanine containing peptides
  作者：Sarah A. Burrage、Tony Raynham、Mark Bradley

  DOI：10.1016/s0040-4039(98)00258-5

  日期：1998.4

  A routine method for the synthesis of dehydroalanine containing peptides has been developed. These residues are introduced as S-methyl cysteines which are subsequently oxidised and eliminated. The approach is compatible with both Boc and Fmoc protection strategies and can allow the introduction of a number of alpha beta unsaturated amino acids into peptides during synthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.