(20R,22R)-9α,14α-epoxy-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-25-hydroxy-5β-cholest-7-en-6-one | 667865-64-7

• 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: (20R,22R)-9α,14α-epoxy-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-25-hydroxy-5β-cholest-7-en-6-one
• 英文别名: 9-dehydro-14-desoxy-9α,14α-epoxy-20-hydroxyecdysone 2,3:20,22-diacetonide；9α,14α-epoxy-14-deoxy-20-hydroxyecdysone diacetonide；20-hydroxy-14-deoxy-9α-15α-epoxyecdysone diacetonine；(20R,22R)-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-9α,14α-epoxy-25-hydroxy-5β-cholest-7-en-6-one；(1S,2S,4S,8R,10R,14S,17S,18R)-17-[(4R,5R)-5-(3-hydroxy-3-methylbutyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]-2,6,6,18-tetramethyl-5,7,21-trioxahexacyclo[12.6.1.01,13.02,10.04,8.014,18]henicos-12-en-11-one
• CAS: 667865-64-7
• 化学式: C₃₃H₅₀O₇
• 分子量: 558.756
• InChiKey: LBLBJOVIBXZTHC-ONGHWOMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  40.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (20R,22R)-9α,14α-epoxy-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-25-hydroxy-5β-cholest-7-en-6-one 在 aluminum oxide 、 sodium tetrahydroborate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 6.0h， 生成 (20R,22R)-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-9α,25-dihydroxy-5β-cholest-7,14-dien-6-one
  参考文献：
  名称：

  Transformation of 9α,14α-epoxy-14-deoxy-20-hydroxyecdysone diacetonide into 25-hydroxydachryhainansterone

  摘要：

  9 alpha,14 alpha-epoxy-14-deoxy-20-hydroxyecdysone diacetonideon treatment with NaBH4 undergoes reduction of 6-keto group and cleavage of allylic oxetane ring, the 6-keto reduction is accompanied by beta ->alpha epimerization of the adjacent HC5 centre. Subsequent re-oxidation of the 6-CHOH fragment into ketone with pyridinium chlorochromate and acidic deprotection affords 25-hydroxydachryhainansterone possessing beta-HC5 configuration due to the re-epimerisation at this centre

  DOI：

  10.1016/j.mencom.2010.09.019
• 作为产物：
  描述：

  脱皮甾酮 2,3:20,22-二缩丙酮 在 氨 、 lithium 、 氧气 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以75%的产率得到(20R,22R)-9α,14α-epoxy-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-25-hydroxy-5β-cholest-7-en-6-one
  参考文献：
  名称：

  Novel ecdysteroid analogs with oxygen-containing heterocycles in the steroid skeleton

  摘要：

  The reaction of ecdysteroids (20-hydroxyecdysone and its acetonides) with lithium in liquid ammonia gave novel analogs with an oxetane 9 alpha,14 alpha-oxacycle in the steroid skeleton. In aqueous alcohol solution the 9,14-oxa analogs rearrange to the more stable 9 alpha,13 alpha-oxa analogs through a 1,2-migration of the 18-Me group from the C-13 to the C-14 atom.

  DOI：

  10.1007/s10593-008-0157-7

文献信息

• Unexpected formation of an oxetane cycle by oxidation of diacetonide of 20-hydroxyecdysone with oxygen in an alkaline medium
  作者：Victor N. Odinokov、Ilgiz V. Galyautdinov、Aliya Sh. Ibragimova、Natalya A. Veskina、Leonard M. Khalilov、Fedor M. Dolgushin、Zoya A. Starikova

  DOI：10.1016/j.mencom.2008.09.023

  日期：2008.9

  The diacetonides of 9 alpha,14 alpha-epoxy-14-deoxy-20-hydroxyecdysone and 14 alpha-hydroperoxy-14-deoxy-20-hydroxyecdysone have been obtained by the interaction of diacetonide of 20-hydroxyecdysone with a solution of lithium in liquid ammonia and following treatment with ammonia chloride and atmospheric oxygen.
• Synthesis of ecdysteroids with migrated group H3C 18
  作者：N. A. Ves’kina、V. N. Odinokov

  DOI：10.1134/s1070428011050162

  日期：2011.5

  Acid-catalyzed rearrangement of oxetane ring in oxetanoecdysteroids and their 7,8 alpha-dihydroanalogs made it possible to synthesize ecdysteroids with H3C18 group migrated from C-13 to C-14 atom.