(5S,8S,11R,14S,17R,20S,22aS)-5,11-Dibenzyl-8,14-bis-hydroxymethyl-17-isopropyl-20-((S)-1-triisopropylsilanyloxy-ethyl)-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone | 184296-08-0

• 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: (5S,8S,11R,14S,17R,20S,22aS)-5,11-Dibenzyl-8,14-bis-hydroxymethyl-17-isopropyl-20-((S)-1-triisopropylsilanyloxy-ethyl)-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone
• 英文别名: (3S,6S,9R,12S,15R,18S,21S)-3,9-dibenzyl-6,12-bis(hydroxymethyl)-15-propan-2-yl-18-[(1S)-1-tri(propan-2-yl)silyloxyethyl]-1,4,7,10,13,16,19-heptazabicyclo[19.3.0]tetracosane-2,5,8,11,14,17,20-heptone
• CAS: 184296-08-0
• 化学式: C₄₇H₇₁N₇O₁₀Si
• 分子量: 922.207
• InChiKey: YPVQDEPKESMGIM-KTETVAMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  65
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  245
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (5S,8S,11R,14S,17R,20S,22aS)-5,11-Dibenzyl-8,14-bis-hydroxymethyl-17-isopropyl-20-((S)-1-triisopropylsilanyloxy-ethyl)-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone 在 伯吉斯试剂 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (1S,4R,8S,11S,17S,20S,23R)-4,11-dibenzyl-23-propan-2-yl-20-[(1S)-1-tri(propan-2-yl)silyloxyethyl]-6,25-dioxa-3,10,13,19,22,27,28-heptazatetracyclo[22.2.1.15,8.013,17]octacosa-5(28),24(27)-diene-2,9,12,18,21-pentone
  参考文献：
  名称：

  Total Synthesis and Assignment of Configuration of Lissoclinamide 7

  摘要：

  The first total synthesis of lissoclinamide 7, a 21-membered cyclopeptide isolated from Lissoclinum bistratum, was accomplished in 23 steps and 4.4% overall yield. The extraordinary configurational lability of the thiazoline segments was overcome by a novel strategy combining the use of the Burgess reagent for multiple simultaneous oxazoline and thiazoline formations and an efficient oxazoline --> thiazoline heterocycle interconversion. In addition to the total synthesis, this work highlights the scope of alternative strategies toward Lissoclinum peptides and presents the preparation of analogues for SAR studies of the cytotoxic effects of this family of marine natural products.

  DOI：

  10.1021/ja962859f
• 作为产物：
  描述：

  (5S,8S,11R,14S,17R,20S,22aS)-5,11-Dibenzyl-8,14-bis-(tert-butyl-dimethyl-silanyloxymethyl)-17-isopropyl-20-((S)-1-triisopropylsilanyloxy-ethyl)-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 以73%的产率得到(5S,8S,11R,14S,17R,20S,22aS)-5,11-Dibenzyl-8,14-bis-hydroxymethyl-17-isopropyl-20-((S)-1-triisopropylsilanyloxy-ethyl)-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone
  参考文献：
  名称：

  Total Synthesis and Assignment of Configuration of Lissoclinamide 7

  摘要：

  The first total synthesis of lissoclinamide 7, a 21-membered cyclopeptide isolated from Lissoclinum bistratum, was accomplished in 23 steps and 4.4% overall yield. The extraordinary configurational lability of the thiazoline segments was overcome by a novel strategy combining the use of the Burgess reagent for multiple simultaneous oxazoline and thiazoline formations and an efficient oxazoline --> thiazoline heterocycle interconversion. In addition to the total synthesis, this work highlights the scope of alternative strategies toward Lissoclinum peptides and presents the preparation of analogues for SAR studies of the cytotoxic effects of this family of marine natural products.

  DOI：

  10.1021/ja962859f