O-methoxymethyl-ergosterol | 95307-27-0

• 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: O-methoxymethyl-ergosterol
• 英文别名: 3β-methoxymethoxyergosta-5,7,22-triene；3-(methoxymethyloxy)-ergosta-5,7,22-triene；(3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3-(methoxymethoxy)-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene
• CAS: 95307-27-0
• 化学式: C₃₀H₄₈O₂
• 分子量: 440.71
• InChiKey: VATACWFFCWWCHC-COQVWLROSA-N

物化性质

• 沸点：
  509.7±50.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-methoxymethyl-ergosterol 在 吡啶 、 Li₂CuCl₃ 、 Mycobacterium sp 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 9.0h， 生成 (3S,9S,10R,13R,14R,17R)-17-((R)-1,5-Dimethyl-hex-5-enyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
  参考文献：
  名称：

  Two Syntheses of FF-MAS

  摘要：

  Follicular fluid-meiosis activating sterol (FF-MAS) has been shown to be an efficient inducer of meiotic maturation. It can potentially be used for improvements of in vitro fertilization techniques. Two short synthesis of FF-MAS are presented in this article. Both syntheses are based on microbiological degradations of sterol side chains. FF-MAS can be synthesized in nine steps from commercially available starting materials by both routes.

  DOI：

  10.1021/ol0343156
• 作为产物：
  描述：

  二甲醇缩甲醛 、 麦角固醇 在 phosphorus pentoxide 作用下， 以100%的产率得到O-methoxymethyl-ergosterol
  参考文献：
  名称：

  Two Syntheses of FF-MAS

  摘要：

  Follicular fluid-meiosis activating sterol (FF-MAS) has been shown to be an efficient inducer of meiotic maturation. It can potentially be used for improvements of in vitro fertilization techniques. Two short synthesis of FF-MAS are presented in this article. Both syntheses are based on microbiological degradations of sterol side chains. FF-MAS can be synthesized in nine steps from commercially available starting materials by both routes.

  DOI：

  10.1021/ol0343156

文献信息

• Selective reduction of the 7(8)-double bond in ergosterol
  作者：Derek H. R. Barton、Xavier Lusinchi、L�on Magdzinski、Jesus Sandoval Ramirez

  DOI：10.1039/c39840001236

  日期：——

  Reduction of ergosterol alkoxide derivatives with lithium metal gives better yields of the 7(8)-reduced product brassicasterol than previous procedures; the mixed products of the reduction are easily converted into ergosta-2,22-dien-6-one, a convenient intermediate for brassinolide synthesis.

  用锂金属还原麦角甾醇的醇盐衍生物比以前的方法得到的7（8）还原的产物芸苔甾醇具有更好的收率。还原的混合产物很容易转化为ergosta-2,22-dien-6-one，这是油菜素内酯合成的便捷中间体。
• Microbial side-chain degradation of ergosterol and its 3-substituted derivatives: A new route for obtaining of deltanoids
  作者：Dmitry V. Dovbnya、Olga V. Egorova、Marina V. Donova

  DOI：10.1016/j.steroids.2010.04.001

  日期：2010.10

  The strain of Mycobacterium sp. VKM Ac-1815D was found to convert ergosterol and its 3-acetate mainly to androst-4-ene-3,17-dione (AD) thus demonstrating ability to reduce 7(8)-double bond and hydrolyze sterol ester in addition to oxidation of 3beta-hydroxy group, Delta(5)-Delta(4) isomerization and side-chain degradation. Ergosterol bioconversion in the presence of isoflavones and ions of some bivalent

  分枝杆菌菌株。发现 VKM Ac-1815D 可将麦角甾醇及其 3-乙酸酯主要转化为雄激素-4-烯-3,17-二酮 (AD)，因此除了氧化外，还展示了还原 7(8)-双键和水解甾醇酯的能力3beta-羟基、Delta(5)-Delta(4) 异构化和侧链降解。在异黄酮和某些二价金属离子（已知的 3β-羟基类固醇脱氢酶抑制剂）存在下，麦角甾醇的生物转化不会改变产品组成。用甲氧基甲基保护麦角甾醇 3beta-羟基允许形成保留 Delta(5,7)-配置的生物转化产品。主要产物通过质谱和质子 NMR 鉴定为 3-甲氧基甲氧基-雄性化合物-5,7-二烯-17-酮 (MA)。发现 MA 产生活性可被甾醇诱导，胆甾酮或石胆酸，但不与脱氢表雄酮、AD、androsta-1,4-ene-3,17-dione 或有机酸。在优化条件下，10g/l O-甲氧基甲基-麦角甾醇（约60%摩尔转化率）120h的MA产
• STEROL DERIVATIVE
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：EP2457923B1

  公开（公告）日：2016-01-27
• Total Synthesis of Agosterol A: an MDR-Modulator from a Marine Sponge
  作者：Nobutoshi Murakami、Masanori Sugimoto、Mari Morita、Motomasa Kobayashi

  DOI：10.1002/1521-3765(20010618)7:12<2663::aid-chem26630>3.0.co;2-u

  日期：2001.6.18

  The first total synthesis of agosterol A, a modulator of multidrug resistance (MDR) mediated by P-gp and MRP1, and isolated from a marine sponge, was achieved from ergosterol by utilizing a regioselective epoxy-cleavage reaction and regioselective dehydroxylation as the key reactions.
• Kondo, Fumihiro; Miyashita, Misako; Konno, Katsuhiro, Journal of the Chemical Society. Perkin transactions I, 1995, # 21, p. 2679 - 2680
  作者：Kondo, Fumihiro、Miyashita, Misako、Konno, Katsuhiro、Takayama, Hiroaki

  DOI：——

  日期：——