(2S,2S)-2-tert-butoxycarbonylamino-3-(4-{4-[4-(2-tert-butoxy-carbonylamino-2-methoxycarbonylethyl)-phenoxy]-but-2-enyloxy}-phenyl)-propionic acid methyl ester | 259268-86-5

• 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: (2S,2S)-2-tert-butoxycarbonylamino-3-(4-{4-[4-(2-tert-butoxy-carbonylamino-2-methoxycarbonylethyl)-phenoxy]-but-2-enyloxy}-phenyl)-propionic acid methyl ester
• 英文别名: methyl (2S)-3-[4-[(E)-4-[4-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]phenoxy]but-2-enoxy]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 259268-86-5
• 化学式: C₃₄H₄₆N₂O₁₀
• 分子量: 642.747
• InChiKey: HSIBKKHLBYQIQZ-SOOYHREHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  46
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Boc-Tyr(All)-OMe 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以67%的产率得到(2S,2S)-2-tert-butoxycarbonylamino-3-(4-{4-[4-(2-tert-butoxy-carbonylamino-2-methoxycarbonylethyl)-phenoxy]-but-2-enyloxy}-phenyl)-propionic acid methyl ester
  参考文献：
  名称：

  Cross-metathesis and ring-closing metathesis reactions of amino acid-based substrates

  摘要：

  Olefin tethers of variable length, introduced into a natural amino acid (side-chain of Ser, Cys; N-terminus of Arg; C-terminus of Phe and Tic; and in both the side-chain and either the N- or C-terminus of Ser, Cys and Tyr), undergo metathesis on treatment with Grubbs' second generation catalyst. Side-chain linked dimers of Ser, Cys and Tyr were obtained by cross-metathesis, while olefin installation at the N- and C-terminus led to dimers of Arg and Phe (or Tic), respectively. Ring-closing metathesis of the doubly alkenylated derivatives of Ser, Cys and Tyr gave 12-, 20- and 24-membered macrocycles. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.043

文献信息

• Cross-metathesis and ring-closing metathesis reactions of amino acid-based substrates
  作者：Andrea J. Vernall、Steven Ballet、Andrew D. Abell

  DOI：10.1016/j.tet.2008.02.043

  日期：2008.4

  Olefin tethers of variable length, introduced into a natural amino acid (side-chain of Ser, Cys; N-terminus of Arg; C-terminus of Phe and Tic; and in both the side-chain and either the N- or C-terminus of Ser, Cys and Tyr), undergo metathesis on treatment with Grubbs' second generation catalyst. Side-chain linked dimers of Ser, Cys and Tyr were obtained by cross-metathesis, while olefin installation at the N- and C-terminus led to dimers of Arg and Phe (or Tic), respectively. Ring-closing metathesis of the doubly alkenylated derivatives of Ser, Cys and Tyr gave 12-, 20- and 24-membered macrocycles. (c) 2008 Elsevier Ltd. All rights reserved.