methyl (2S)-2-[2-((2S)-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido)-3-methylpropanamido]-4-methylpentanoate | 259217-27-1

• 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: methyl (2S)-2-[2-((2S)-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido)-3-methylpropanamido]-4-methylpentanoate
• 英文别名: Z-Val-Aib-Leu-OMe；methyl (2S)-4-methyl-2-[[2-methyl-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoyl]amino]pentanoate
• CAS: 259217-27-1
• 化学式: C₂₄H₃₇N₃O₆
• 分子量: 463.574
• InChiKey: ZBIGBBLABIRJKC-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  33.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  122.83
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[2-((2S)-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido)-3-methylpropanamido]-4-methylpentanoate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 (S)-2-[2-((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-2-methyl-propionylamino]-4-methyl-pentanoic acid
  参考文献：
  名称：

  Synthesis of Endothiopeptides and Their Cyclization to 1,3-Thiazol-5(4H)-imines

  摘要：

  Further investigations of the synthesis of endothio analogues of the segment 1-10 (8) of an apolar analogon of zervamicin IIA are described. The endothiodecapeptide Boc-Trp-Ile-Ala-Aib-Ile-Val-Aib-Leu-Aib-Psi(CS)-Pro-OMe (10) has been prepared in good yield by our novel methodology. On the other hand, all attempts to prepare endothio analogues of 8 with the thioamide group at position 3 (Ala') gave not the expected linear endothiopeptides but led to epimerized 1,3-thiazol-5(4H)-imine derivatives as the main products. The mixture of epimers of the thiazolimines 27, 30, and 31 have been separated by means of preparative HPLC, and their structures have been established by 2D-NMR experiments.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<1899::aid-hlca1899>3.0.co;2-m
• 作为产物：
  描述：

  benzyl N-{(1S)-2-methyl-1-[({1,1-dimethyl-2-[methyl(phenyl)amino]-2-oxoethyl}amino)carbonyl]propyl}carbamate 在 盐酸 、 水 、 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 17.0h， 生成 methyl (2S)-2-[2-((2S)-{[(benzyloxy)carbonyl]amino}-3-methylbutanamido)-3-methylpropanamido]-4-methylpentanoate
  参考文献：
  名称：

  Synthesis of Endothiopeptides and Their Cyclization to 1,3-Thiazol-5(4H)-imines

  摘要：

  Further investigations of the synthesis of endothio analogues of the segment 1-10 (8) of an apolar analogon of zervamicin IIA are described. The endothiodecapeptide Boc-Trp-Ile-Ala-Aib-Ile-Val-Aib-Leu-Aib-Psi(CS)-Pro-OMe (10) has been prepared in good yield by our novel methodology. On the other hand, all attempts to prepare endothio analogues of 8 with the thioamide group at position 3 (Ala') gave not the expected linear endothiopeptides but led to epimerized 1,3-thiazol-5(4H)-imine derivatives as the main products. The mixture of epimers of the thiazolimines 27, 30, and 31 have been separated by means of preparative HPLC, and their structures have been established by 2D-NMR experiments.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<1899::aid-hlca1899>3.0.co;2-m