(22R,23R,24R)-2α,3,22,23-tetrahydroxy-24-methyl-5α-cholestan-6-one | 121468-16-4

• 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: (22R,23R,24R)-2α,3,22,23-tetrahydroxy-24-methyl-5α-cholestan-6-one
• 英文别名: (22R,23R,24R)-2α,3β-22,23-tetrahydroxy-5α-ergostan-6-one；3,24-bisepi-castasterone；3,24-diepicastasterone；24-epi-castasterone；(2R,3R,5S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R,4R,5R)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-2,3-dihydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
• CAS: 121468-16-4
• 化学式: C₂₈H₄₈O₅
• 分子量: 464.686
• InChiKey: VYUIKSFYFRVQLF-ZTLCDWFCSA-N

物化性质

• 熔点：
  211-213 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  598.7±50.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (22R,23R,24R)-2α,3,22,23-tetrahydroxy-24-methyl-5α-cholestan-6-one 在 Ornithopus sativus 作用下， 生成 2α,3β,6β-trihydroxy-5α-pregnane-20-one
  参考文献：
  名称：

  Pregnane-type metabolites of brassinosteroids in cell suspension cultures of Ornithopus sativus

  摘要：

  Exogenously applied 24-epi-castasterone and 24-epi-brassinolide are transformed in a multi-step metabolic process by cell suspension cultures of Ornithopus sativus to give 2 alpha,3 beta,6 beta-trihydroxy-5 alpha-pregnane-20-one and 2 alpha,3 beta-dihydroxy-B-homo-7-oxa-5 alpha-pregnane-6,20-dione, respectively, as the major metabolites. This is the first report concerning a catabolic side-chain degradation of brassinosteroids in plant material.

  DOI：

  10.1016/s0031-9422(00)89794-0
• 作为产物：
  描述：

  Ergostan-6-one, 2,3,22,23-tetrakis(acetyloxy)-, (2a,3a,5a,22R,23R)- 在 sodium tetrahydroborate 、 palladium on activated charcoal 、 水 、 氢气 、 四丁基碘化铵 、 二正丁基氧化锡 、 potassium carbonate 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， -25.0~110.0 ℃ 、101.33 kPa 条件下， 反应 21.5h， 生成 (22R,23R,24R)-2α,3,22,23-tetrahydroxy-24-methyl-5α-cholestan-6-one
  参考文献：
  名称：

  Synthesis of ergostane-type brassinosteroids with modifications in ring A

  摘要：

  在此，我们提出了一种新的策略，用于制备一系列不同环A片段的植物甾醇生物合成前体/代谢物。该方案基于使用易得的植物激素（具有2α,3α-二醇基团的表油菜素或表油脂酮）作为起始材料。所需的官能团（Δ2-，2α,3α-和2β,3β-环氧基，2α,3β-，2β,3α-和2β,3β-二羟基，3-酮基，3α-和3β-羟基，2α-羟基-3-酮基）可以从2α,3α-二醇中通过几个简单步骤合成（Corey-Winter反应，环氧化，氧化，氢化还原等）。

  DOI：

  10.3762/bjoc.13.229

文献信息

• Synthesis of 2,24-Diepicastasterone and 3,24-Diepicastasterone as Potential Brassinosteroid Metabolites of the Cockroach Periplaneta americana
  作者：Brunhilde Voigt、Andrea Porzel、Günter Adam、Dieter Golsch、Waldemar Adam、Christoph Wagner、Kurt Merzweiler

  DOI：10.1135/cccc20020091

  日期：——

  Investigations of the metabolic conversion of the phytohormone 24-epicastasterone (1) in the cockroach Periplaneta americana (L.) required the synthesis of 2,24-diepicastasterone (4), 3,24-diepicastasterone (7b) and 2-dehydro-3,24-diepicastasterone (9) as reference standards. 2,24-Diepicastasterone (4) was synthesized from 2α,3α-epoxy derivative 2 as well as from the 2β,3β-epoxy-22,23-diol 3 by acid-catalyzed water addition to the epoxy function leading to the desired 2β,3α-trans functionality. 3,24-Diepicastasterone (7b) was prepared by NaBH₄-reduction of the 3-oxo derivative 6. Upon deprotection conditions from the ketol acetonides 6 and 8 in both cases 2-dehydro-3,24-diepicastasterone (9) was obtained. The structure of 2,24-diepicastasterone (4) was confirmed by X-ray analysis.

  对植物激素24-epicastasterone (1)在美洲蠊（Periplaneta americana (L.)）中的代谢转化的研究需要合成2,24-diepicastasterone (4)、3,24-diepicastasterone (7b)和2-dehydro-3,24-diepicastasterone (9)作为参考标准。2,24-diepicastasterone (4)由2α,3α-环氧衍生物2和2β,3β-环氧-22,23-二醇3经酸催化加水反应制得，得到所需的2β,3α-trans官能团。3,24-diepicastasterone (7b)通过NaBH₄还原3-酮衍生物6制备而成。在去保护酮醇丙酮酸酯6和8的条件下，两种情况都得到2-dehydro-3,24-diepicastasterone (9)。2,24-diepicastasterone (4)的结构经过X射线分析得到证实。
• Levinson, Edward E.; Traven, Valery F., Journal of Chemical Research - Part S, 1996, # 4, p. 196 - 197
  作者：Levinson, Edward E.、Traven, Valery F.

  DOI：——

  日期：——
• Preparation and synthetic application of partially protected brassinosteroids
  作者：Vladimir A. Khripach、Vladimir N. Zhabinskii、Yuliya Y. Zhiburtovich、Galina V. Ivanova、Olga V. Konstantinova、Dmitrii V. Tsavlovskii、Sybille Lorenz、Bernd Schneider

  DOI：10.1016/j.steroids.2009.09.010

  日期：2010.1

  Preparation of partially protected brassinosteroids is achieved through the reaction of the source material (24-epicastasterone and 24-epibrassinolide) with diol-specific reagents (2,2-dimethoxypropane and methylboronic acid). The obtained products were shown to be useful synthetic intermediates for further preparation of minor representatives of this class of natural phytohormones (such as 3 24, diepicastasterone and 3-dehydro-24-epibrassinolide). (C) 2009 Elsevier Inc. All rights reserved.
• Synthesis of ergostane-type brassinosteroids with modifications in ring A
  作者：Vladimir N Zhabinskii、Darya A Osiyuk、Yuri V Ermolovich、Natalia M Chaschina、Tatsiana S Dalidovich、Miroslav Strnad、Vladimir A Khripach

  DOI：10.3762/bjoc.13.229

  日期：——

  Herein, we present a new strategy for the preparation of a broad range of brassinosteroid biosynthetic precursors/metabolites differing by the ring A fragment. The protocol is based on the use of readily available phytohormones of this class bearing a 2α,3α-diol moiety (epibrassinolide or epicastasterone) as starting materials. The required functionalities (Δ²-, 2α,3α- and 2β,3β-epoxy-, 2α,3β-, 2β,3α-, and 2β,3β-dihydroxy-, 3-keto-, 3α- and 3β-hydroxy-, 2α-hydroxy-3-keto-) were synthesized from 2α,3α-diols in a few simple steps (Corey–Winter reaction, epoxidation, oxidation, hydride reduction, etc.).

  在此，我们提出了一种新的策略，用于制备一系列不同环A片段的植物甾醇生物合成前体/代谢物。该方案基于使用易得的植物激素（具有2α,3α-二醇基团的表油菜素或表油脂酮）作为起始材料。所需的官能团（Δ2-，2α,3α-和2β,3β-环氧基，2α,3β-，2β,3α-和2β,3β-二羟基，3-酮基，3α-和3β-羟基，2α-羟基-3-酮基）可以从2α,3α-二醇中通过几个简单步骤合成（Corey-Winter反应，环氧化，氧化，氢化还原等）。
• Pregnane-type metabolites of brassinosteroids in cell suspension cultures of Ornithopus sativus
  作者：A. Kolbe、B. Schneider、A. Porzel、B. Voigt、G. Krauss、G. Adam

  DOI：10.1016/s0031-9422(00)89794-0

  日期：1994.6

  Exogenously applied 24-epi-castasterone and 24-epi-brassinolide are transformed in a multi-step metabolic process by cell suspension cultures of Ornithopus sativus to give 2 alpha,3 beta,6 beta-trihydroxy-5 alpha-pregnane-20-one and 2 alpha,3 beta-dihydroxy-B-homo-7-oxa-5 alpha-pregnane-6,20-dione, respectively, as the major metabolites. This is the first report concerning a catabolic side-chain degradation of brassinosteroids in plant material.