(3S,6S,7R,12S,15R,18S,21S,22R)-15-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,12,18-triisopropyl-7,9,9,22,24,24-hexamethyl-8,23-dioxa-1,4,10,13,16,19-hexaaza-tricyclo[19.3.0.0^6,10]tetracosane-2,5,11,14,17,20-hexaone | 820226-11-7

• 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: (3S,6S,7R,12S,15R,18S,21S,22R)-15-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,12,18-triisopropyl-7,9,9,22,24,24-hexamethyl-8,23-dioxa-1,4,10,13,16,19-hexaaza-tricyclo[19.3.0.0^6,10]tetracosane-2,5,11,14,17,20-hexaone
• 英文别名: (3S,6S,7R,12S,15R,18S,21S,22R)-15-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-7,9,9,22,24,24-hexamethyl-3,12,18-tri(propan-2-yl)-8,23-dioxa-1,4,10,13,16,19-hexazatricyclo[19.3.0.06,10]tetracosane-2,5,11,14,17,20-hexone
• CAS: 820226-11-7
• 化学式: C₃₉H₇₀N₆O₉Si
• 分子量: 795.105
• InChiKey: FQVVDLFDQAEZIZ-SSUWPBJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  55
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  185
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3S,6S,7R,12S,15R,18S,21S,22R)-15-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,12,18-triisopropyl-7,9,9,22,24,24-hexamethyl-8,23-dioxa-1,4,10,13,16,19-hexaaza-tricyclo[19.3.0.0^6,10]tetracosane-2,5,11,14,17,20-hexaone 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 72.0h， 以79%的产率得到(3S,6S,9S,12S,15R,18S)-3,9,15-Tris-((R)-1-hydroxy-ethyl)-6,12,18-triisopropyl-1,4,7,10,13,16-hexaaza-cyclooctadecane-2,5,8,11,14,17-hexaone
  参考文献：
  名称：

  Pseudoprolines as Removable Turn Inducers:  Tools for the Cyclization of Small Peptides

  摘要：

  The cyclization of small peptides which do not incorporate turn inducers is often difficult. We have developed a method involving the use of removable turn inducers, in the form of pseudoprolines, for the cyclization of difficult peptide sequences. The pseudoprolines induce a cisoid amide bond in the peptide backbone which facilitates cyclization. They are then readily removed to yield a cyclic peptide that does not contain any turn inducers.

  DOI：

  10.1021/jo0484732
• 作为产物：
  描述：

  Cbz-Val-Thr-OMe 在 palladium on activated charcoal N-甲基吗啉 、 咪唑 、 lithium hydroxide 、 五氟苯基二苯基磷酸酯 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 57.0h， 生成 (3S,6S,7R,12S,15R,18S,21S,22R)-15-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,12,18-triisopropyl-7,9,9,22,24,24-hexamethyl-8,23-dioxa-1,4,10,13,16,19-hexaaza-tricyclo[19.3.0.0^6,10]tetracosane-2,5,11,14,17,20-hexaone
  参考文献：
  名称：

  Pseudoprolines as Removable Turn Inducers:  Tools for the Cyclization of Small Peptides

  摘要：

  The cyclization of small peptides which do not incorporate turn inducers is often difficult. We have developed a method involving the use of removable turn inducers, in the form of pseudoprolines, for the cyclization of difficult peptide sequences. The pseudoprolines induce a cisoid amide bond in the peptide backbone which facilitates cyclization. They are then readily removed to yield a cyclic peptide that does not contain any turn inducers.

  DOI：

  10.1021/jo0484732

文献信息

• Pseudoprolines as Removable Turn Inducers:  Tools for the Cyclization of Small Peptides
  作者：Danielle Skropeta、Katrina A. Jolliffe、Peter Turner

  DOI：10.1021/jo0484732

  日期：2004.12.1

  The cyclization of small peptides which do not incorporate turn inducers is often difficult. We have developed a method involving the use of removable turn inducers, in the form of pseudoprolines, for the cyclization of difficult peptide sequences. The pseudoprolines induce a cisoid amide bond in the peptide backbone which facilitates cyclization. They are then readily removed to yield a cyclic peptide that does not contain any turn inducers.