methyl (9S,12S,15S)-12-benzyl-15-[(2-methylpropan-2-yl)oxycarbonylamino]-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.13,7]docosa-1(19),3,5,7(22),17,20-hexaene-9-carboxylate | 172035-51-7

• 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 (9S,12S,15S)-12-benzyl-15-[(2-methylpropan-2-yl)oxycarbonylamino]-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.13,7]docosa-1(19),3,5,7(22),17,20-hexaene-9-carboxylate
• CAS: 172035-51-7
• 化学式: C₃₃H₃₇N₃O₇
• 分子量: 587.673
• InChiKey: QDJLIDPZEUNBKJ-KCHLEUMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (9S,12S,15S)-12-benzyl-15-[(2-methylpropan-2-yl)oxycarbonylamino]-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.13,7]docosa-1(19),3,5,7(22),17,20-hexaene-9-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 (9S,12S,15S)-15-Amino-12-benzyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-9-carboxylic acid methyl ester; hydrochloride
  参考文献：
  名称：

  A Cyclic Side-Chain-Linked Biphenyl Ether Tripeptide: H3N+-cyclo-[Phe(4−O)-Phe-Phe(3−O)]-OMe.Cl−

  摘要：

  The crystal structure of the chloride salt of H3N(+)-cyclo-(Phe(4-O)-Phe-Phe((3)-O))-OMe, cyclo- phenylalanyl-phenylalanyl-phenylalaninium chloride methyl esther, C28H30N3O5+Cl- is described. It is oxidatively linked through a biaryl ether linkage formed from the hydroxyl of 4-hydroxyphenylalanine and the meta position of the distal phenylalanine residue, This is the first reported crystal-structure determination of a cyclic 17-membered biphenyl ether tripeptide, a class which includes the natural products K-13 and OF4949 I-IV, An unusual C--H ... O hydrogen bond is formed between the methine H atom of the N-terminal C alpha and a carbonyl-O atom of a neighboring molecule [C ... O = 2.995 (4) Angstrom].

  DOI：

  10.1107/s0108270196009262
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 2,6-di-tert-butylphenoxide anion 作用下， 生成 methyl (9S,12S,15S)-12-benzyl-15-[(2-methylpropan-2-yl)oxycarbonylamino]-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.13,7]docosa-1(19),3,5,7(22),17,20-hexaene-9-carboxylate
  参考文献：
  名称：

  A Cyclic Side-Chain-Linked Biphenyl Ether Tripeptide: H3N+-cyclo-[Phe(4−O)-Phe-Phe(3−O)]-OMe.Cl−

  摘要：

  The crystal structure of the chloride salt of H3N(+)-cyclo-(Phe(4-O)-Phe-Phe((3)-O))-OMe, cyclo- phenylalanyl-phenylalanyl-phenylalaninium chloride methyl esther, C28H30N3O5+Cl- is described. It is oxidatively linked through a biaryl ether linkage formed from the hydroxyl of 4-hydroxyphenylalanine and the meta position of the distal phenylalanine residue, This is the first reported crystal-structure determination of a cyclic 17-membered biphenyl ether tripeptide, a class which includes the natural products K-13 and OF4949 I-IV, An unusual C--H ... O hydrogen bond is formed between the methine H atom of the N-terminal C alpha and a carbonyl-O atom of a neighboring molecule [C ... O = 2.995 (4) Angstrom].

  DOI：

  10.1107/s0108270196009262

文献信息

• Total Synthesis of the Cyclic Biphenyl Ether Peptides K-13 and OF4949-III <i>via</i> S_NAr Macrocyclization of Peptidyl Ruthenium π-Arene Complexes
  作者：James W. Janetka、Daniel H. Rich

  DOI：10.1021/ja970614c

  日期：1997.7.1

  yield by biaryl ether formation from peptidyl ruthenium complexes. Direct comparisons between these two approaches are provided. Transition metal π-complexes of either N-protected or carboxyl-protected amino acids can be used as coupling partners in peptide coupling reactions. Preformed peptidyl ruthenium complexes can be used to synthesize cyclic biphenyl ethers in a combinatorial fashion.

  预先形成的钌环戊二烯基阳离子肽基 π 配合物的分子内亲核芳香取代 (SNAr) 在方便、高产的反应中形成环状联苯醚。两种天然产物 K-13 和 OF4949-III 的高效收敛全合成证明了该方法的实用性。以高收率合成了 K-13 和 OF4949-I-IV 的几种类似物，并且通过由肽基钌配合物形成联芳醚以高收率形成了一个无法通过大环内酰胺化方法制备的环系统。提供了这两种方法之间的直接比较。N-保护或羧基保护的氨基酸的过渡金属π-复合物可用作肽偶联反应中的偶联伙伴。
• Janetka, James W.; Rich, Daniel H., Journal of the American Chemical Society, 1995, vol. 117, # 42, p. 10585 - 10586
  作者：Janetka, James W.、Rich, Daniel H.

  DOI：——

  日期：——