(22R,23R)-3β,22,23-trihydroxycholest-5-ene | 77790-41-1

• 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)-3β,22,23-trihydroxycholest-5-ene
• 英文别名: (22R),(23R)-dihydroxycholesterol；(22r,23r)-22,23-Dihydroxycholesterol；(2S,3R,4R)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylheptane-3,4-diol
• CAS: 77790-41-1
• 化学式: C₂₇H₄₆O₃
• 分子量: 418.66
• InChiKey: DIRYUPAZMXIPTE-WBYRFXTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (22R,23R)-3β,22,23-trihydroxycholest-5-ene 在 吡啶 、 sodium hydroxide 、 重铬酸吡啶 、 硼烷四氢呋喃络合物 、 双氧水 、 对甲苯磺酸 、 lithium bromide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (22S,23S)-22,-23-isopropylidenedioxy-5α-cholest-2-en-6-one
  参考文献：
  名称：

  Synthesis of 28-norbrassinolide.

  摘要：

  28-Norbrassinolide (2α, 3α, 22R, 23R-tetrahydroxy-B-homo-7-oxa-5α-cholestan-6-one) 是植物生长促进类固醇内酯 brassinolide 的类似物，由 22R，23R-二羟基胆固醇合成。此外，还介绍了 22，23-二羟基胆固醇的其他 C-22，23 立体异构体的合成。

  DOI：

  10.1248/cpb.29.903
• 作为产物：
  描述：

  (22R,23R)-3β,22,23-trihydroxycholest-5-ene 3,22-dimethoxymethyl ether 在 盐酸 、 甲醇 作用下， 以80%的产率得到(22R,23R)-3β,22,23-trihydroxycholest-5-ene
  参考文献：
  名称：

  Stereocontrol of three contiguous chiral centers of brassinosteroid side chain by using .alpha.-alkoxy organoleads

  摘要：

  The reaction of steroidal aldehyde 2 with chiral alpha-methoxyorganolead (S)-3 in the presence of TiCl4 gave the Cram-syn product 4, a precursor of 28-norbrassinolide, in 90% yield as a single stereoisomer. A kinetic resolution was observed in the TiCl4 mediated reaction of 2 with (+/-)-3; again 4 was produced in 99% yield as a single isomer.

  DOI：

  10.1021/jo00037a002

文献信息

• Stereoselective synthesis of plant growth-prompting steroids, brassinolide, castasterone, typhasterol, and their 28-nor analogues
  作者：Suguru Takatsuto、Naoto Yazawa、Masaji Ishiguro、Masuo Morisaki、Nobuo Ikekawa

  DOI：10.1039/p19840000139

  日期：——

  Plant growth-promoting steroids, brassinolide (1a), (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one, castasterone (2a), (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-5α-ergo-stan-6-one, 28-norbrassinolide (1b), (22R,23R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-chole-stan-6-one, brassinone (2b), (22R,23R)-2α,3α,22,23-tetrahydroxy-5α-cholestan-6-one, and typh-asterol (2c), (22R,23R,24S)-3α

  促进植物生长的类固醇，油菜素内酯（1a），（22 R，23 R，24 S）-2α，3α，22,23-四羟基-B -homo-7-oxa-5α-ergostan-6-one，卡司他酮（ 2a），（22 R，23 R，24 S）-2α，3α，22,23-四羟基-5α-麦角甾烷-6-一，28-去甲油菜素内酯（1b），（22 R，23 R）-2α ，3α，22,23-tetrahydroxy- B -homo-7-oxa-5α-hole-stan-6-，brasinone（2b），（22 R，23 R）-2α，3α，22,23-tetrahydroxy- 5α-胆甾醇-6-1和伤寒甾醇（2c），（22 R，23 R，24 S）-3α，22,23-三羟基-5α.-麦角甾醇-6-，已被立体选择性地合成。这些类固醇在三种不同的生物测定法中显示出非常强的生物学活性。
• Acyclic stereocontrol based on chelation-controlled ene reaction with chiral α- and β-alkoxyaldehydes
  作者：Koichi Mikami、Teck-Peng Loh、Takeshi Nakai

  DOI：10.1016/s0957-4166(00)82265-x

  日期：1990.1
• Takatsuto, Suguru; Ikekawa, Nobuo, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 7, p. 3006 - 3010
  作者：Takatsuto, Suguru、Ikekawa, Nobuo

  DOI：——

  日期：——
• TAKATSUTO, SUGURU;IKEKAWA, NOBUO, CHEM. AND PHARM. BULL., 35,(1987) N 7, 3006-3010
  作者：TAKATSUTO, SUGURU、IKEKAWA, NOBUO

  DOI：——

  日期：——
• Roots and shoots of tomato produce 6-deoxo-28-norcathasterone, 6-deoxo-28-nortyphasterol and 6-deoxo-28-norcastasterone, possible precursors of 28-norcastasterone
  作者：Takao Yokota、Tatsuro Sato、Yasutomo Takeuchi、Takahito Nomura、Koyuru Uno、Tsuyoshi Watanabe、Suguru Takatsuto

  DOI：10.1016/s0031-9422(01)00237-0

  日期：2001.9

  Roots and shoots of tomato (Lycopersicon esculentum) were investigated for the occurrence of biosynthetic precursors of 28-norcastasterone, a C-27 brassinosteroid that we have shown to be present in shoots of tomato. A series of putative precursors, including 6-deoxo-28-norcathasterone, 6-deoxo-28-norteasterone, 3-dehydro-6-deoxo-28-norteasterone, 6-deoxo-28-nortyphasterol and 6-deoxo-28-norcastasterone, were synthesized and used as GC-MS standards, resulting in the identification of 6-deoxo-28-norcathasterone, 6-deoxo-28-nortyphasterol and 6-deoxo-28-norcastasterone in both roots and shoots. These findings indicate that the biosynthesis of 28-norcastasterone may parallel that of castasterone. The endogenous levels of brassinosteroids differed between roots and shoots, indicating that the biosynthesis of brassinosteroids is differently regulated between these tissues. Regulation of root growth by brassinosteroids is also discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.