prop-2-enyl (E,4S)-4-[[(2R,3S)-3-methyl-2-[[(3S)-3-[[(2S)-1-[(2S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(2-trimethylsilylethoxycarbonylamino)propanoyl]pyrrolidine-2-carbonyl]amino]-2-oxo-6-[phenylmethoxycarbonyl-[(E)-N'-phenylmethoxycarbonylcarbamimidoyl]amino]hexanoyl]amino]pentanoyl]amino]-5-[4-tri(propan-2-yl)silyloxyphenyl]pent-2-enoate | 475503-59-4

• 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
• 英文名称: prop-2-enyl (E,4S)-4-[[(2R,3S)-3-methyl-2-[[(3S)-3-[[(2S)-1-[(2S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(2-trimethylsilylethoxycarbonylamino)propanoyl]pyrrolidine-2-carbonyl]amino]-2-oxo-6-[phenylmethoxycarbonyl-[(E)-N'-phenylmethoxycarbonylcarbamimidoyl]amino]hexanoyl]amino]pentanoyl]amino]-5-[4-tri(propan-2-yl)silyloxyphenyl]pent-2-enoate
• CAS: 475503-59-4
• 化学式: C₇₁H₁₀₅N₉O₁₆Si₂
• 分子量: 1396.84
• InChiKey: MBRSIFMPYVIHAE-DRMCBEJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.16
• 重原子数：
  98
• 可旋转键数：
  42
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  331
• 氢给体数：
  6
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  prop-2-enyl (E,4S)-4-[[(2R,3S)-3-methyl-2-[[(3S)-3-[[(2S)-1-[(2S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(2-trimethylsilylethoxycarbonylamino)propanoyl]pyrrolidine-2-carbonyl]amino]-2-oxo-6-[phenylmethoxycarbonyl-[(E)-N'-phenylmethoxycarbonylcarbamimidoyl]amino]hexanoyl]amino]pentanoyl]amino]-5-[4-tri(propan-2-yl)silyloxyphenyl]pent-2-enoate 在 四(三苯基膦)钯 苯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以86%的产率得到
  参考文献：
  名称：

  Application of cyano ylide methodology to the synthesis of cyclotheonamides E2 and E3

  摘要：

  A total synthesis of cyclotheonamides E-2 and E-3 is reported. A key step in the synthesis involves the formation of the alpha-keto amide linkage by application of the cyano ylide activation of a carboxyl group as developed in our earlier syntheses of cyclic peptide protease inhibitors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00627-0
• 作为产物：
  描述：

  benzyl (2S)-1-[(2S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(2-trimethylsilylethoxycarbonylamino)propanoyl]pyrrolidine-2-carboxylate 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 臭氧 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 prop-2-enyl (E,4S)-4-[[(2R,3S)-3-methyl-2-[[(3S)-3-[[(2S)-1-[(2S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(2-trimethylsilylethoxycarbonylamino)propanoyl]pyrrolidine-2-carbonyl]amino]-2-oxo-6-[phenylmethoxycarbonyl-[(E)-N'-phenylmethoxycarbonylcarbamimidoyl]amino]hexanoyl]amino]pentanoyl]amino]-5-[4-tri(propan-2-yl)silyloxyphenyl]pent-2-enoate
  参考文献：
  名称：

  Application of cyano ylide methodology to the synthesis of cyclotheonamides E2 and E3

  摘要：

  A total synthesis of cyclotheonamides E-2 and E-3 is reported. A key step in the synthesis involves the formation of the alpha-keto amide linkage by application of the cyano ylide activation of a carboxyl group as developed in our earlier syntheses of cyclic peptide protease inhibitors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00627-0

文献信息

• Application of cyano ylide methodology to the synthesis of cyclotheonamides E2 and E3
  作者：Harry H Wasserman、Rui Zhang

  DOI：10.1016/s0040-4020(02)00627-0

  日期：2002.8

  A total synthesis of cyclotheonamides E-2 and E-3 is reported. A key step in the synthesis involves the formation of the alpha-keto amide linkage by application of the cyano ylide activation of a carboxyl group as developed in our earlier syntheses of cyclic peptide protease inhibitors. (C) 2002 Elsevier Science Ltd. All rights reserved.