(1S,3R,5S,6R,8S,10R,12S,13R)-12-methyl-5,13-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-12-(3-phenylmethoxypropyl)-2,7,11-trioxatricyclo[8.5.0.03,8]pentadecane | 436153-74-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,5S,6R,8S,10R,12S,13R)-12-methyl-5,13-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-12-(3-phenylmethoxypropyl)-2,7,11-trioxatricyclo[8.5.0.03,8]pentadecane
• CAS: 436153-74-1
• 化学式: C₄₅H₅₄O₇
• 分子量: 706.92
• InChiKey: HNACBCRKKRZINK-SLQBJWMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,3R,5S,6R,8S,10R,12S,13R)-12-methyl-5,13-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-12-(3-phenylmethoxypropyl)-2,7,11-trioxatricyclo[8.5.0.03,8]pentadecane 在 palladium dihydroxide 氢气 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4aR,5aS,6aR,8S,9R,11aS,12aR,13aS)-8-(3-Hydroxy-propyl)-2-(4-methoxy-phenyl)-8-methyl-dodecahydro-1,3,5,7,12-pentaoxa-cyclohepta[b]anthracen-9-ol
  参考文献：
  名称：

  Studies toward the Total Synthesis of Gymnocin A, a Cytotoxic Polyether:  A Highly Convergent Entry to the F−N Ring Fragment

  摘要：

  [GRAPHICS]An efficient and highly convergent synthesis of the FGHIJKLMN ring fragment of gymnocin A, a cyctotoxic polycyclic ether isolated from the notorious red-tide forming dinoflagellate Gymnodinium mikimotoi, has been achieved. The present synthesis relied on extensive use of the B-alkyl Suzuki-Miyaura coupling reaction.

  DOI：

  10.1021/ol025814u
• 作为产物：
  描述：

  (2R,6R,7S)-2-[[(2S,3R,5S,6R)-3-[tert-butyl(dimethyl)silyl]oxy-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]methyl]-7-methyl-6-phenylmethoxy-7-(3-phenylmethoxypropyl)oxepan-3-one 在 三乙基硅烷 、 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 (1S,3R,5S,6R,8S,10R,12S,13R)-12-methyl-5,13-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-12-(3-phenylmethoxypropyl)-2,7,11-trioxatricyclo[8.5.0.03,8]pentadecane
  参考文献：
  名称：

  Studies toward the Total Synthesis of Gymnocin A, a Cytotoxic Polyether:  A Highly Convergent Entry to the F−N Ring Fragment

  摘要：

  [GRAPHICS]An efficient and highly convergent synthesis of the FGHIJKLMN ring fragment of gymnocin A, a cyctotoxic polycyclic ether isolated from the notorious red-tide forming dinoflagellate Gymnodinium mikimotoi, has been achieved. The present synthesis relied on extensive use of the B-alkyl Suzuki-Miyaura coupling reaction.

  DOI：

  10.1021/ol025814u

文献信息

• Studies toward the Total Synthesis of Gymnocin A, a Cytotoxic Polyether:  A Highly Convergent Entry to the F−N Ring Fragment
  作者：Makoto Sasaki、Chihiro Tsukano、Kazuo Tachibana

  DOI：10.1021/ol025814u

  日期：2002.5.1

  [GRAPHICS]An efficient and highly convergent synthesis of the FGHIJKLMN ring fragment of gymnocin A, a cyctotoxic polycyclic ether isolated from the notorious red-tide forming dinoflagellate Gymnodinium mikimotoi, has been achieved. The present synthesis relied on extensive use of the B-alkyl Suzuki-Miyaura coupling reaction.