(2S,3S,4S,5R,6S)-3-(benzoyloxy)-5-bromo-2-methyl-6-(((2aS,4R,5'R,6aS,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-5-oxodocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl)oxy)tetrahydro-2H-pyran-4-yl ethyl malonate | 848854-48-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S,4S,5R,6S)-3-(benzoyloxy)-5-bromo-2-methyl-6-(((2aS,4R,5'R,6aS,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-5-oxodocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl)oxy)tetrahydro-2H-pyran-4-yl ethyl malonate
• CAS: 848854-48-8
• 化学式: C₄₅H₆₁BrO₁₁
• 分子量: 857.877
• InChiKey: FQLARZNZGKSWGL-ILLZFXQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  57.0
• 可旋转键数：
  8.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  132.89
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6S)-3-(benzoyloxy)-5-bromo-2-methyl-6-(((2aS,4R,5'R,6aS,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-5-oxodocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl)oxy)tetrahydro-2H-pyran-4-yl ethyl malonate 在 sodium hydride 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 6.0h， 以128 mg的产率得到
  参考文献：
  名称：

  Preparation of an analogue of orbicuside A, an unusual cardiac glycoside

  摘要：

  A steroid containing a multi-linked glycoside, analogous to the bufadienolide orbicuside A, has been prepared. The key steps were (i) the preparation of a 2alpha-allyloxycarbonyloxy-3beta-hydroxy steroid, (ii) a Ferrier reaction between the steroid and a rhamnal derivative, (iii) removal of protecting group and oxidation of the 2-hydroxy group, (iv) dihydroxylation of the pseudoglycal from the sterically more hindered side and finally (v) ring closure by acetal formation under acidic conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.028
• 作为产物：
  描述：

  (25R)-5a-螺甾烷-3-酮 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,2-双(二苯基膦)乙烷 吡啶 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 三氟化硼乙醚 、 水 、 二甲基二环氧乙烷 、 戴斯-马丁氧化剂 、 六甲基二硅氮烷 、 环氧氯丙烷 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 80.41h， 生成 (2S,3S,4S,5R,6S)-3-(benzoyloxy)-5-bromo-2-methyl-6-(((2aS,4R,5'R,6aS,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-5-oxodocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl)oxy)tetrahydro-2H-pyran-4-yl ethyl malonate
  参考文献：
  名称：

  Preparation of an analogue of orbicuside A, an unusual cardiac glycoside

  摘要：

  A steroid containing a multi-linked glycoside, analogous to the bufadienolide orbicuside A, has been prepared. The key steps were (i) the preparation of a 2alpha-allyloxycarbonyloxy-3beta-hydroxy steroid, (ii) a Ferrier reaction between the steroid and a rhamnal derivative, (iii) removal of protecting group and oxidation of the 2-hydroxy group, (iv) dihydroxylation of the pseudoglycal from the sterically more hindered side and finally (v) ring closure by acetal formation under acidic conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.028