(3R)-4-[(2R,4S,6S)-4-acetyloxy-6-methoxy-6-[[(2S,6R)-6-[(E)-3-[(2S,3S,4E,6S)-2-methoxy-4-(2-methoxy-2-oxoethylidene)-6-[(2R,3R)-2-[(4-methoxyphenyl)methoxy]-3-(phenylmethoxymethoxy)butyl]-3-[(2E,4E)-octa-2,4-dienoyl]oxyoxan-2-yl]-3-methylbut-1-enyl]-4-methylideneoxan-2-yl]methyl]-5,5-dimethyloxan-2-yl]-3-hydroxybutanoic acid | 1190429-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3R)-4-[(2R,4S,6S)-4-acetyloxy-6-methoxy-6-[[(2S,6R)-6-[(E)-3-[(2S,3S,4E,6S)-2-methoxy-4-(2-methoxy-2-oxoethylidene)-6-[(2R,3R)-2-[(4-methoxyphenyl)methoxy]-3-(phenylmethoxymethoxy)butyl]-3-[(2E,4E)-octa-2,4-dienoyl]oxyoxan-2-yl]-3-methylbut-1-enyl]-4-methylideneoxan-2-yl]methyl]-5,5-dimethyloxan-2-yl]-3-hydroxybutanoic acid
• CAS: 1190429-44-7
• 化学式: C₆₃H₈₈O₁₈
• 分子量: 1133.38
• InChiKey: UUIFZGKFIIFFRU-FRJHTANSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  81
• 可旋转键数：
  33
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  220
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  三乙基氯硅烷 、 (3R)-4-[(2R,4S,6S)-4-acetyloxy-6-methoxy-6-[[(2S,6R)-6-[(E)-3-[(2S,3S,4E,6S)-2-methoxy-4-(2-methoxy-2-oxoethylidene)-6-[(2R,3R)-2-[(4-methoxyphenyl)methoxy]-3-(phenylmethoxymethoxy)butyl]-3-[(2E,4E)-octa-2,4-dienoyl]oxyoxan-2-yl]-3-methylbut-1-enyl]-4-methylideneoxan-2-yl]methyl]-5,5-dimethyloxan-2-yl]-3-hydroxybutanoic acid 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以4.4 mg的产率得到(R)-4-((2S,4S,6S)-4-acetoxy-6-(((2S,6R)-6-((E)-3-((2S,3S,6S,E)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(4-methoxybenzyloxy)butyl)-2-methoxy-4-(2-methoxy-2-oxoethylidene)-3-((2E,4E)-octa-2,4-dienoyloxy)tetrahydro-2H-pyran-2-yl)-3-methylbut-1-enyl)-4-methylenetetrahydro-2H-pyran-2-yl)methyl)-6-methoxy-5,5-dimethyltetrahydro-2H-pyran-2-yl)-3-(triethylsilyloxy)butanoic acid
  参考文献：
  名称：

  Substitution on the A-Ring Confers to Bryopyran Analogues the Unique Biological Activity Characteristic of Bryostatins and Distinct From That of the Phorbol Esters

  摘要：

  A close structural analogue of bryostatin 1, which differs from bryostatin 1 only by the absence of the C-30 carbomethoxy group (on the C-13 enoate of the B-ring), has been prepared by total synthesis. Biological assays reveal a crucial role for substitution in the bryostatin 1 A-ring in conferring those responses which are characteristic of bryostatin 1 and distinct from those observed with PMA.

  DOI：

  10.1021/ol8027253
• 作为产物：
  描述：

  (2E,4E)-((2S,3S,6S,E)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-acetoxy-6-((R)-4-(tert-butylthio)-2-hydroxy-4-oxobutyl)-2-methoxy-3,3-dimethyltetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(4-methoxybenzyloxy)butyl)-2-methoxy-4-(2-methoxy-2-oxoethylidene)tetrahydro-2H-pyran-3-yl) octa-2,4-dienoate 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 (3R)-4-[(2R,4S,6S)-4-acetyloxy-6-methoxy-6-[[(2S,6R)-6-[(E)-3-[(2S,3S,4E,6S)-2-methoxy-4-(2-methoxy-2-oxoethylidene)-6-[(2R,3R)-2-[(4-methoxyphenyl)methoxy]-3-(phenylmethoxymethoxy)butyl]-3-[(2E,4E)-octa-2,4-dienoyl]oxyoxan-2-yl]-3-methylbut-1-enyl]-4-methylideneoxan-2-yl]methyl]-5,5-dimethyloxan-2-yl]-3-hydroxybutanoic acid
  参考文献：
  名称：

  Substitution on the A-Ring Confers to Bryopyran Analogues the Unique Biological Activity Characteristic of Bryostatins and Distinct From That of the Phorbol Esters

  摘要：

  A close structural analogue of bryostatin 1, which differs from bryostatin 1 only by the absence of the C-30 carbomethoxy group (on the C-13 enoate of the B-ring), has been prepared by total synthesis. Biological assays reveal a crucial role for substitution in the bryostatin 1 A-ring in conferring those responses which are characteristic of bryostatin 1 and distinct from those observed with PMA.

  DOI：

  10.1021/ol8027253