cyclo--5-methylheptanoyl>oxy-3-(methoxymethoxy)-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl> | 126587-65-3

• 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-(methoxymethoxy)-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl>
• 英文别名: tert-butyl N-[(3S,6S,7S,8S,12S,13R,16S,17R,20S,23S)-13-[(2S)-butan-2-yl]-7-(methoxymethoxy)-20-[(4-methoxyphenyl)methyl]-6,17,21-trimethyl-3-(2-methylpropyl)-2,5,10,15,19,22-hexaoxo-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: 126587-65-3
• 化学式: C₅₈H₉₉N₅O₁₄Si
• 分子量: 1118.53
• InChiKey: FSTPJHRQDMGRKU-GDTXZXKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  78
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  227
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  cyclo--5-methylheptanoyl>oxy-3-(methoxymethoxy)-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl> 在 二甲基溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到cyclo--5-methylheptanoyl>oxy-3-hydroxy-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
• 作为产物：
  描述：

  (2S,3S,4S)-4-[(3S,4R,5S)-4-[[(2S,3R)-3-[(2S)-2-[[(2S)-1-[(2S)-2-amino-4-methylpentanoyl]pyrrolidine-2-carbonyl]-methylamino]-3-(4-methoxyphenyl)propanoyl]oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]-5-methyl-3-tri(propan-2-yl)silyloxyheptanoyl]oxy-3-(methoxymethoxy)-2,5-dimethylhexanoic acid 在 五氟苯基二苯基磷酸酯 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以68%的产率得到cyclo--5-methylheptanoyl>oxy-3-(methoxymethoxy)-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl>
  参考文献：
  名称：

  二肽合成中偶联试剂选择的比较研究

  摘要：

  摘要 对所选偶联试剂在二肽合成中的有效性进行了比较研究。研究中包括一种新的偶联试剂，五氟苯基二苯基次膦酸盐 (FDPP, 1)、苯并三唑-1-基-氧基三(二甲氨基) 六氟磷酸鏻(BOP, 2)、2-(1H-苯并三唑-1-基)-1， 1,3,3-四甲基六氟磷酸盐 (HBTU, 3) 和氯甲酸异丁酯 (IBCF, 4)。我们发现 BOP (2) 提供了最高的收率和最低的外消旋化限制。

  DOI：

  10.1080/00397919308009787

文献信息

• Synthesis of New Didemnin B Analogs for Investigations of Structure/Biological Activity Relationships
  作者：Scott C. Mayer、Joshi Ramanjulu、Matthew D. Vera、Amy J. Pfizenmayer、Madeleine M. Joullie

  DOI：10.1021/jo00097a022

  日期：1994.9

  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.
• 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：——