Carbonic acid (2R,6R)-6-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-7-((2R,3R,4R,5S,6R)-3-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-2-methyl-heptyl ester methyl ester | 202462-21-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: Carbonic acid (2R,6R)-6-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-7-((2R,3R,4R,5S,6R)-3-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-2-methyl-heptyl ester methyl ester
• CAS: 202462-21-3
• 化学式: C₅₆H₇₇N₃O₉
• 分子量: 936.242
• InChiKey: OXKYLFYBJREMPP-JFOUTLAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.02
• 重原子数：
  68.0
• 可旋转键数：
  20.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  150.67
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Carbonic acid (2R,6R)-6-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-7-((2R,3R,4R,5S,6R)-3-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-2-methyl-heptyl ester methyl ester 在 重铬酸吡啶 、 4 A molecular sieve 、 camphor-10-sulfonic acid 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.7h， 生成 (2R,6R)-6-((5R,7R,8R,9S,10S,13R,14S,17R)-7-(((2R,3R,4R,5S,6R)-3-azido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-3,3-dimethoxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methylheptyl methyl carbonate
  参考文献：
  名称：

  Synthesis of pavoninin-1, a shark repellent substance, and its structural analogues toward mechanistic studies on their membrane perturbation

  摘要：

  Pavoninin-1 (1), which was isolated from a defense secretion of the sole Pardachirus spp. as an ichthyotoxic and a shark repellent principle, and its structural analogue 2 were synthesized, where glycosylation using an 2-azidoglycosyl sulfoxide (10) afforded the corresponding beta-glycoside exclusively in high yield. Introduction of the alpha,beta-unsaturated ketone system in the ring A of 1 was achieved by phenylselenenylation of dihydropavoninin-1 (3) and subsequent oxidative elimination without protection of the hydroxyl groups in the sugar portion. The mode of action of these glycosides was evaluated for their perturbation on phosphatidylcholine liposomal membrane, using the fluorescent dye leakage method. The results revealed that membrane affinity does not parallel membrane perturbation but rather compensates it, and the spatial arrangement of hydrophobic and hydrophilic regions within a molecule is likely to reflect on the difference in potency of action among them. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00170-3
• 作为产物：
  描述：

  在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 3.5h， 以96%的产率得到Carbonic acid (2R,6R)-6-[(3R,5S,7R,8R,9S,10S,13R,14S,17R)-7-((2R,3R,4R,5S,6R)-3-azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-2-methyl-heptyl ester methyl ester
  参考文献：
  名称：

  Synthesis of pavoninin-1, a shark repellent substance, and its structural analogues toward mechanistic studies on their membrane perturbation

  摘要：

  Pavoninin-1 (1), which was isolated from a defense secretion of the sole Pardachirus spp. as an ichthyotoxic and a shark repellent principle, and its structural analogue 2 were synthesized, where glycosylation using an 2-azidoglycosyl sulfoxide (10) afforded the corresponding beta-glycoside exclusively in high yield. Introduction of the alpha,beta-unsaturated ketone system in the ring A of 1 was achieved by phenylselenenylation of dihydropavoninin-1 (3) and subsequent oxidative elimination without protection of the hydroxyl groups in the sugar portion. The mode of action of these glycosides was evaluated for their perturbation on phosphatidylcholine liposomal membrane, using the fluorescent dye leakage method. The results revealed that membrane affinity does not parallel membrane perturbation but rather compensates it, and the spatial arrangement of hydrophobic and hydrophilic regions within a molecule is likely to reflect on the difference in potency of action among them. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00170-3