(S)-2-[2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionylamino)-2-(pyridin-2-ylsulfanyl)-acetylamino]-4-methyl-pentanoic acid methyl ester | 817625-07-3

• 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-[2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionylamino)-2-(pyridin-2-ylsulfanyl)-acetylamino]-4-methyl-pentanoic acid methyl ester
• 英文别名: Boc-Ser(Bn)-DL-Ncy(pyrid-2-yl)-Leu-OMe；methyl (2S)-4-methyl-2-[[2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoyl]amino]-2-pyridin-2-ylsulfanylacetyl]amino]pentanoate
• CAS: 817625-07-3
• 化学式: C₂₉H₄₀N₄O₇S
• 分子量: 588.725
• InChiKey: FLFZLOZNOKGPOP-PFXBLUCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4,8-anhydro-5,6,7,9-tetra-O-benzyl-1,3-dideoxy-D-glycero-D-gulo-non-2-ulose 、 (S)-2-[2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionylamino)-2-(pyridin-2-ylsulfanyl)-acetylamino]-4-methyl-pentanoic acid methyl ester 在 nickel(II) iodide samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到(S)-2-[2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionylamino)-3-hydroxy-3-methyl-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-butyrylamino]-4-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  An improved protocol for the SmI2-promoted C-alkylation of peptides: degradation and functionalization of serine residues in linear and cyclic peptides

  摘要：

  The utility of the samarium diiodide promoted C-alkylation of peptides for the introduction of new side chains on peptide strands is dramatically enhanced by the initial oxidative degradation of serine residues in small peptides. In this way, cyclic peptides may also be included in this repertoire as a method for the preparation of peptide libraries. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.024
• 作为产物：
  描述：

  (S)-2-[(S)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionylamino)-3-hydroxy-propionylamino]-4-methyl-pentanoic acid methyl ester 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 (S)-2-[2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionylamino)-2-(pyridin-2-ylsulfanyl)-acetylamino]-4-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  An improved protocol for the SmI2-promoted C-alkylation of peptides: degradation and functionalization of serine residues in linear and cyclic peptides

  摘要：

  The utility of the samarium diiodide promoted C-alkylation of peptides for the introduction of new side chains on peptide strands is dramatically enhanced by the initial oxidative degradation of serine residues in small peptides. In this way, cyclic peptides may also be included in this repertoire as a method for the preparation of peptide libraries. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.024