Acetic acid (2S,4aS,4bS,6R,6aR,6bR,7S,8S,9aS,10bR,12aS)-2-acetoxy-8-((1R,3R)-1-acetoxy-4-hydroxy-3-methyl-butyl)-4a,6a,7-trimethyl-2,3,4,4a,4b,5,6,6a,6b,7,8,9a,10b,11,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthren-6-yl ester | 571185-85-8

• 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: Acetic acid (2S,4aS,4bS,6R,6aR,6bR,7S,8S,9aS,10bR,12aS)-2-acetoxy-8-((1R,3R)-1-acetoxy-4-hydroxy-3-methyl-butyl)-4a,6a,7-trimethyl-2,3,4,4a,4b,5,6,6a,6b,7,8,9a,10b,11,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthren-6-yl ester
• CAS: 571185-85-8
• 化学式: C₃₃H₅₀O₈
• 分子量: 574.755
• InChiKey: OLVYOGCYRNNDTP-NBVCTFJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  41.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,4aS,4bS,6R,6aR,6bR,7S,8S,9aS,10bR,12aS)-2-acetoxy-8-((1R,3R)-1-acetoxy-4-hydroxy-3-methyl-butyl)-4a,6a,7-trimethyl-2,3,4,4a,4b,5,6,6a,6b,7,8,9a,10b,11,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthren-6-yl ester 在 potassium carbonate 咪唑 、 potassium osmate(VI) 、 Hydroquinone 1,4-phthalazinediyl diether 、 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 27.5h， 生成 Acetic acid (2S,4aS,4bS,6R,6aR,6bR,7S,8S,9aS,10bR,12aS)-2-acetoxy-8-((1R,3R)-4-acetoxy-1,3-dihydroxy-3-methyl-butyl)-4a,6a,7-trimethyl-2,3,4,4a,4b,5,6,6a,6b,7,8,9a,10b,11,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthren-6-yl ester
  参考文献：
  名称：

  New Oxidative Tools for the Functionalization of the Cephalostatin North 1 Hemisphere

  摘要：

  Dimethyldioxirane (DMDO) C-H oxidation of ketone 17 to hemiketal 18 (82%), bis-dehydration to vinyl ether 21 (77%), and DMDO again provides C-23 axial alcohol 23 (99%). Routine processing, Including a double-stereoselective Sharpless AD reaction (de >98%), gives alcohols 7 and 32. C-23 deoxy substrate 7 undergoes Suarez hypoiodite oxidative cyclization to (natural) beta spiroketal 34, but compound 32, bearing a C-23 silyl ether, generates unnatural spiroketal 33.

  DOI：

  10.1021/ol034551g
• 作为产物：
  描述：

  (25R)-3β-Acetoxy-14-hydroxy-5α,14β-spirostan-12-on 在 吡啶 、 三乙基硅烷 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 二甲基二环氧乙烷 、 苯硒酚 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 224.17h， 生成 Acetic acid (2S,4aS,4bS,6R,6aR,6bR,7S,8S,9aS,10bR,12aS)-2-acetoxy-8-((1R,3R)-1-acetoxy-4-hydroxy-3-methyl-butyl)-4a,6a,7-trimethyl-2,3,4,4a,4b,5,6,6a,6b,7,8,9a,10b,11,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthren-6-yl ester
  参考文献：
  名称：

  New Oxidative Tools for the Functionalization of the Cephalostatin North 1 Hemisphere

  摘要：

  Dimethyldioxirane (DMDO) C-H oxidation of ketone 17 to hemiketal 18 (82%), bis-dehydration to vinyl ether 21 (77%), and DMDO again provides C-23 axial alcohol 23 (99%). Routine processing, Including a double-stereoselective Sharpless AD reaction (de >98%), gives alcohols 7 and 32. C-23 deoxy substrate 7 undergoes Suarez hypoiodite oxidative cyclization to (natural) beta spiroketal 34, but compound 32, bearing a C-23 silyl ether, generates unnatural spiroketal 33.

  DOI：

  10.1021/ol034551g