(20R,22R)-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-9α,25-dihydroxy-5β-cholest-7,14-dien-6-one | 667865-67-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (20R,22R)-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-9α,25-dihydroxy-5β-cholest-7,14-dien-6-one
• 英文别名: 9α-hydroxystachisterone B 2,3:20,22-diacetonide；9α-hydroxystachysterone B 2,3:20,22-diacetonide；9α-hydroxystachysterone B diacetonide；(20R,22R)-9α,25-dihydroxy-2β,3β:20,22-bis(isopropylidenedioxy)-5β-cholesta-7,14-dien-6-one；9α-hydroxystachysterone C
• CAS: 667865-67-0
• 化学式: C₃₃H₅₀O₇
• 分子量: 558.756
• InChiKey: CQNRQUXLZQSNFX-HTVXVVGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  40.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  94.45
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (20R,22R)-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-9α,25-dihydroxy-5β-cholest-7,14-dien-6-one 在 甲醇 、 sodium 、 palladium 10% on activated carbon 、 氢气 作用下， 反应 3.5h， 以90%的产率得到(20R,22R)-9α,25-dihydroxy-2β,3β:20,22-diisopropylidenedioxy-5β,8α-cholestan-6-one
  参考文献：
  名称：

  Synthesis of 7,8α-dihydro-14α-deoxyecdysteroids

  摘要：

  A Pd-C-catalyzed hydrogenation in methanol and in the presence of sodium methylate is a simple, convenient and high yielding reduction method to convert the 7,14-dien-6-one ecdysteroids to their corresponding 7,8 alpha-dihydro-14 alpha-deoxyecdysteroids. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.02.027
• 作为产物：
  描述：

  (20R,22R)-6β,9α,25-trihydroxy-2β,3β:20,22-bis[(dimethylmethylene)dioxy]-5α-cholesta-7,14-diene 在 aluminum oxide 、 pyridinium chlorochromate 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以83%的产率得到(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

文献信息

• Novel ecdysteroid analogs with oxygen-containing heterocycles in the steroid skeleton
  作者：V. N. Odinokov、I. V. Galyautdinov、A. Sh. Ibragimova、N. A. Veskina、L. M. Khalilov、F. M. Dolgushin、Z. A. Starikova

  DOI：10.1007/s10593-008-0157-7

  日期：2008.9

  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.
• 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.