(4aS,4a'S,10aR,10a'R,13S,13'S,16R,16'R,18aS,18a'S,23bR,23b'R,24aS,24a'S,27R,27'R)-16,16'-bis((1S)-1-((tert-butyl(dimethyl)silyl)oxy)ethyl)-21,21'-dichloro-23b,23b'-dihydroxy-13,13'-bis(methoxymethyl)-27,27'-di(propane-2-yl)-2,2',3,3',4,4',4a,4a',8,8',9,9',10,10',10a,10a',12,12',13,13',15,15',16,16',19,19',23b,23b',24,24',24a,24a',26,26',27,27'-hexatriacontahydro-18aH,18a'H-22,22'-bidipyridazino[1'',6'':10',11';1''',6''':7',8'][1,4,7,10,13,16]hexaazacyclooctadecino[1',2':1,5]pyrrolo[2,3-b]indole-5,5',11,11',14,14',17,17',25,25',28,28'(1H,1'H,7H,7'H)-dodecone | 1248759-51-4

• 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: (4aS,4a'S,10aR,10a'R,13S,13'S,16R,16'R,18aS,18a'S,23bR,23b'R,24aS,24a'S,27R,27'R)-16,16'-bis((1S)-1-((tert-butyl(dimethyl)silyl)oxy)ethyl)-21,21'-dichloro-23b,23b'-dihydroxy-13,13'-bis(methoxymethyl)-27,27'-di(propane-2-yl)-2,2',3,3',4,4',4a,4a',8,8',9,9',10,10',10a,10a',12,12',13,13',15,15',16,16',19,19',23b,23b',24,24',24a,24a',26,26',27,27'-hexatriacontahydro-18aH,18a'H-22,22'-bidipyridazino[1'',6'':10',11';1''',6''':7',8'][1,4,7,10,13,16]hexaazacyclooctadecino[1',2':1,5]pyrrolo[2,3-b]indole-5,5',11,11',14,14',17,17',25,25',28,28'(1H,1'H,7H,7'H)-dodecone
• 英文别名: (1S,4R,11S,18R,21S,24R,27S,35R)-24-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-32-[(1S,4R,11S,18R,21S,24R,27S,35R)-24-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-31-chloro-35-hydroxy-21-(methoxymethyl)-2,5,12,19,22,25-hexaoxo-4-propan-2-yl-3,6,7,13,14,20,23,26,28-nonazahexacyclo[24.10.0.06,11.013,18.027,35.029,34]hexatriaconta-29(34),30,32-trien-32-yl]-31-chloro-35-hydroxy-21-(methoxymethyl)-4-propan-2-yl-3,6,7,13,14,20,23,26,28-nonazahexacyclo[24.10.0.06,11.013,18.027,35.029,34]hexatriaconta-29(34),30,32-triene-2,5,12,19,22,25-hexone
• CAS: 1248759-51-4
• 化学式: C₈₀H₁₂₂Cl₂N₁₈O₁₈Si₂
• 分子量: 1751.04
• InChiKey: UZLQLERMTADAOV-ZQLVLQNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  120
• 可旋转键数：
  15
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  446
• 氢给体数：
  14
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  (4aS,4a'S,10aR,10a'R,13S,13'S,16R,16'R,18aS,18a'S,23bR,23b'R,24aS,24a'S,27R,27'R)-16,16'-bis((1S)-1-((tert-butyl(dimethyl)silyl)oxy)ethyl)-21,21'-dichloro-23b,23b'-dihydroxy-13,13'-bis(methoxymethyl)-27,27'-di(propane-2-yl)-2,2',3,3',4,4',4a,4a',8,8',9,9',10,10',10a,10a',12,12',13,13',15,15',16,16',19,19',23b,23b',24,24',24a,24a',26,26',27,27'-hexatriacontahydro-18aH,18a'H-22,22'-bidipyridazino[1'',6'':10',11';1''',6''':7',8'][1,4,7,10,13,16]hexaazacyclooctadecino[1',2':1,5]pyrrolo[2,3-b]indole-5,5',11,11',14,14',17,17',25,25',28,28'(1H,1'H,7H,7'H)-dodecone 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到chloptosin
  参考文献：
  名称：

  完全合成胰蛋白酶

  摘要：

  有两个总比一个好：一种新的不对称制备嵌入的哌嗪酸的有机催化路线和邻氯吡咯并吲哚的Stille偶联是二聚环肽类胰蛋白酶的全合成的关键步骤（参见结构）。

  DOI：

  10.1002/anie.201002880
• 作为产物：
  描述：

  (2S,2'S)-2,2'-((((2S,2'S,3aR,3a'R,8aS,8a'S)-1,1'-bis((2R,3S)-2-amino)-3-((tert-butyl(dimethyl)silyl)oxy)butanoyl)-6,6'-dichloro-3a,3a'-dihydroxy-1,1',2,2',3,3',3a,3a',8,8',8a,8a'-dodecahydro-5,5'-bipyrrolo[2,3-b]indole-2,2'-diyl)bis(carbonylimino((2R)-3-methyl-1-oxobutane-2,1-diyl)(6S)tetrahydropyridazine-1,6(2H)-diylcarbonyl(6R)tetrahydropyridazine-1,6(2H)-diylcarbonylimino))bis(3-methoxypropanioc acid) 在 N-羟基-7-氮杂苯并三氮唑 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4aS,4a'S,10aR,10a'R,13S,13'S,16R,16'R,18aS,18a'S,23bR,23b'R,24aS,24a'S,27R,27'R)-16,16'-bis((1S)-1-((tert-butyl(dimethyl)silyl)oxy)ethyl)-21,21'-dichloro-23b,23b'-dihydroxy-13,13'-bis(methoxymethyl)-27,27'-di(propane-2-yl)-2,2',3,3',4,4',4a,4a',8,8',9,9',10,10',10a,10a',12,12',13,13',15,15',16,16',19,19',23b,23b',24,24',24a,24a',26,26',27,27'-hexatriacontahydro-18aH,18a'H-22,22'-bidipyridazino[1'',6'':10',11';1''',6''':7',8'][1,4,7,10,13,16]hexaazacyclooctadecino[1',2':1,5]pyrrolo[2,3-b]indole-5,5',11,11',14,14',17,17',25,25',28,28'(1H,1'H,7H,7'H)-dodecone
  参考文献：
  名称：

  完全合成胰蛋白酶

  摘要：

  有两个总比一个好：一种新的不对称制备嵌入的哌嗪酸的有机催化路线和邻氯吡咯并吲哚的Stille偶联是二聚环肽类胰蛋白酶的全合成的关键步骤（参见结构）。

  DOI：

  10.1002/anie.201002880

文献信息

• Total Synthesis of Chloptosin
  作者：Alexander J. Oelke、David J. France、Tatjana Hofmann、Georg Wuitschik、Steven V. Ley

  DOI：10.1002/anie.201002880

  日期：2010.8.16

  one: A new organocatalytic route for the asymmetric preparation of the embedded piperazic acids and a Stille coupling of an ortho‐chloropyrroloindole served as key steps in the total synthesis of the dimeric cyclopeptide chloptosin (see structure).

  有两个总比一个好：一种新的不对称制备嵌入的哌嗪酸的有机催化路线和邻氯吡咯并吲哚的Stille偶联是二聚环肽类胰蛋白酶的全合成的关键步骤（参见结构）。
• Total Synthesis of Chloptosin: A Dimeric Cyclohexapeptide
  作者：Alexander J. Oelke、Francesca Antonietti、Leonardo Bertone、Philippa B. Cranwell、David J. France、Rebecca J. M. Goss、Tatjana Hofmann、Stephan Knauer、Steven J. Moss、Paul C. Skelton、Richard M. Turner、Georg Wuitschik、Steven V. Ley

  DOI：10.1002/chem.201003216

  日期：2011.4.4

  Here we describe in full our investigations into the synthesis of the dimeric cyclohexapeptide chloptosin in 17 linear steps. Particularly, this work features an organocatalytic tandem process for the synthesis of the embedded piperazic acids, in which a differentially protected azodicarboxylate is used together with pyrrolidinyl tetrazole as the catalyst. The central biaryl bond is being formed by

  在这里，我们以17个线性步骤完整地描述了对二聚环六肽chlottosin合成的研究。特别地，该工作的特征在于用于合成嵌入的哌嗪酸的有机催化串联方法，其中将受保护的偶氮二羧酸酯与吡咯烷基四唑一起用作催化剂。中心联芳基键由两个空间上要求的邻氯吡咯并吲哚片段的斯蒂勒偶联形成。合成策略的固有灵活性被证明是有益的，因为可以在合成程序的进行过程中平稳地调整路线。