cyclo--5-methylheptanoyl>oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl> | 129942-52-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: cyclo--5-methylheptanoyl>oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl>
• 英文别名: cyclo-(N-(tert-butoxycarbonyl)-O-{[N-((2S,3S,4S)-4-{(3S,4R,5S)-4-amino-3-[(triisopropylsilyl)oxy]-5-methylheptanoyl}oxy-3-oxo-2,5-dimethylhexanoyl)-L-leucyl]-L-prolyl-N,O-dimethyl-L-tyrosyl}-L-threonyl)；tert-butyl N-[(3S,6S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,7,10,15,19,22-heptaoxo-8-propan-2-yl-12-tri(propan-2-yl)silyloxy-9,18-dioxa-1,4,14,21-tetrazabicyclo[21.3.0]hexacosan-16-yl]carbamate
• CAS: 129942-52-5
• 化学式: C₅₆H₉₃N₅O₁₃Si
• 分子量: 1072.47
• InChiKey: MUMPEIOGAKNXRA-JTLQSGMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.68
• 重原子数：
  75
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  225
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  cyclo--5-methylheptanoyl>oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl> 在 N-甲基吗啉 、 盐酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Synthesis of New Didemnin B Analogs for Investigations of Structure/Biological Activity Relationships

  摘要：

  Modifications were introduced in the side chain of didemnin B to afford several analogs (1f-1j) for biological testing in order to identify the features responsible for the bioactivity of the natural products (1a-1c). To achieve our goal, two changes were made in the proline ring of the beta-turn side chain. Initially, a hydroxyl group was incorporated at the C-4 position of the ring to increase the polar nature of the molecule. Secondly, unsaturation was introduced at C-3 and C-4 to increase the rigidity of the ring and to provide a site for tritiation to follow the drug pathway in biological systems. Improvements were also introduced in the macrocycle construction to produce gram quantities of this unit (1d) for the preparation of the planned analogs. The linear precursor to the macrocycle was oxidized more effectively with 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin periodinane reagent), and cyclization yields were increased substantially by using a new coupling reagent, pentafluorophenyl diphenylphosphinate (FDPP). (1H-1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and pentafluorophenyl trifluoroacetate were also used to improve other coupling reactions.

  DOI：

  10.1021/jo00097a022
• 作为产物：
  描述：

  cyclo--5-methylheptanoyl>oxy-3-hydroxy-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl> 在 二甲基亚砜 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以92%的产率得到cyclo--5-methylheptanoyl>oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl>
  参考文献：
  名称：

  didemnins A、B 和 C 的全合成和结构研究

  摘要：

  Didemnins A、B 和 C 以立体控制的方式有效制备，产生常见的大环，并在单独的步骤中，在 L-苏氨酸的氨基上引入取代基作为光学纯单元。我们设想 L-亮氨酸和 HIP 基团 (2S,4S) 之间以及 L-苏氨酸和异司他汀 (3S,4R,5S) 之间的断开将提供两个单元：HIP-异司他汀单元 (I) 和四肽单元 (II) )

  DOI：

  10.1021/ja00177a030

文献信息

• EWING, WILLIAM R.;HARRIS, BRUCE D.;LI, WEN-REN;JOULLIE, MADELEINE M., TETRAHEDRON LETT., 30,(1989) N9, C. 3757-3760
  作者：EWING, WILLIAM R.、HARRIS, BRUCE D.、LI, WEN-REN、JOULLIE, MADELEINE M.

  DOI：——

  日期：——