(20S)-20-hydroxymethyl-6β-methoxy-3α,5α-cyclopregnane-16β,17α-diol | 285979-67-1

• 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: (20S)-20-hydroxymethyl-6β-methoxy-3α,5α-cyclopregnane-16β,17α-diol
• 英文别名: (1S,2R,5R,7R,8R,10R,11S,13S,14S,15S)-14-[(2R)-1-hydroxypropan-2-yl]-8-methoxy-2,15-dimethylpentacyclo[8.7.0.02,7.05,7.011,15]heptadecane-13,14-diol
• CAS: 285979-67-1
• 化学式: C₂₃H₃₈O₄
• 分子量: 378.552
• InChiKey: SJDVOVHCUPIJID-QULDHVHBSA-N

物化性质

• 沸点：
  489.3±35.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (20S)-20-hydroxymethyl-6β-methoxy-3α,5α-cyclopregnane-16β,17α-diol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 6β-methoxy-23,24,25,26,27-pentanor-3α,5α-cyclofurostane-16α,17α-diol
  参考文献：
  名称：

  Kruszewska, Anna; Wilczewska, Agnieszka Z.; Wojtkielewicz, Agnieszka, Polish Journal of Chemistry, 2006, vol. 80, # 4, p. 611 - 615

  摘要：

  DOI：
• 作为产物：
  描述：

  (20S)-6β-methoxy-17α-hydroxy-3α,5α-cyclopregnane-20,16β-carbolactone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以100%的产率得到(20S)-20-hydroxymethyl-6β-methoxy-3α,5α-cyclopregnane-16β,17α-diol
  参考文献：
  名称：

  某些16α，17α-氧化类固醇与氢过氧化锂反应中的邻近基团参与环氧化物的裂解

  摘要：

  为了找到一种有效的合成抗肿瘤皂苷OSW-1糖苷配基的新方法，用酸，碱和氢过氧化锂处理了16α，17α-氧化类固醇。不论侧链结构如何，酸都会引起Wagner-Meerwein类型的重排。除非存在22-羰基基团，否则16α，17α-环氧化合物证明对碱具有抗性。对于22酯或22酮，环氧化物环会被碱裂解，形成相应的烯丙基醇。用氢过氧化锂将16α，17α-22氧化酯环氧化物环裂解，然后将内酯16β，17α-二羟基酸内酯化。通过内酯与异戊基锂反应获得皂苷OSW-1糖苷配基。

  DOI：

  10.1016/s0040-4020(01)00051-5

文献信息

• Novel Saponin Compounds, Methods of Preparation Thereof, Use Thereof and Pharmaceutical Compositions
  申请人：Morzycki Jacek Witold

  公开号：US20110311652A1

  公开（公告）日：2011-12-22

  This invention relates to novel saponin compounds of formula II wherein MBz denotes p-methoxybenzoyl, and R is selected from the group comprising C 6-10 aryl, C 6-10 aryl-C 1-4 alkyl-, C 1-18 alkanoyl, C 3-18 alkenyl, C 6-10 aryl-C(O)—, C 6-10 aryl-C 1-4 alkyl-C(O)—, wherein each of the groups can optionally be substituted. These compounds possess a selective cytostatic activity, useful, e.g., in the treatment of proliferative diseases. The invention further relates to methods of preparation of the novel compounds and to a pharmaceutical composition containing these compounds.

  本发明涉及式II的新型皂苷化合物，其中MBz表示p-甲氧基苯甲酰基，R选自包括C6-10芳基，C6-10芳基-C1-4烷基，C1-18酰基，C3-18烯基，C6-10芳基-C（O）-，C6-10芳基-C1-4烷基-C（O）-的群，其中每个基均可选择性地被取代。这些化合物具有选择性细胞毒活性，可用于治疗增生性疾病。本发明还涉及制备这些新化合物的方法以及含有这些化合物的制药组合物。
• Practical Method for the Absolute Configuration Assignment of <i>tert</i>/<i>tert</i> 1,2-Diols Using Their Complexes with Mo₂(OAc)₄
  作者：Marcin Górecki、Ewa Jabłońska、Anna Kruszewska、Agata Suszczyńska、Zofia Urbańczyk-Lipkowska、Michael Gerards、Jacek W. Morzycki、Wojciech J. Szczepek、Jadwiga Frelek

  DOI：10.1021/jo062445x

  日期：2007.4.1

  We describe here an application of the practical, simple, and reliable approach for the determination of the absolute configuration of sterically demanding tert/tert vic-diols. According to this method, it is only necessary to mix dimolybdenum tetraacteate and a chiral diol in DMSO and record the CD spectra in the 250-650 nm spectral range. From the sign of the CD bands occurring at around 310, 350, and 400 nm, it is possible to establish the chirality of the diol unit expressed by the sign of the O-C-C-O torsion angle. Because the preferred conformation of the diol in the formed complex is known, we are able to determine the absolute configuration of the carbon atoms in the diol subunit even in flexible tert/tert vic-diols.
• Unusual oxidative transformations of a steroidal 16α,17α,22-triol
  作者：Jacek W. Morzycki、José Oscar H. Pérez-Díaz、Rosa Santillan、Agnieszka Wojtkielewicz

  DOI：10.1016/j.steroids.2009.10.002

  日期：2010.1

  A number of unexpected reactions were observed during attempts to invert configuration at C16 in 16 alpha,17 alpha,22-triol 3a. The PDC oxidation of 3a produced the D-seco-aldehyde 4a. Analogous compound 4b was obtained by Swern oxidation of the 16 alpha,17 alpha-dihydroxy-22-O-TES-ether 3b in addition to the desired 16-ketone 7. The unprotected triol 3a yielded pentacyclic products 5 and 6 under similar conditions. The Mitsunobu reaction of the triol 3a afforded 16-ketone 8 with inverted configuration of the side chain. During heating of a solution of 3a in THF with NaH at reflux autoxidation to the 16-ketone cyclic hemiketal 5, identical to one of the Swern oxidation products, took place. (C) 2009 Elsevier Inc. All rights reserved.
• Morzycki; Gryszkiewicz, Polish Journal of Chemistry, 2001, vol. 75, # 7, p. 983 - 989
  作者：Morzycki、Gryszkiewicz

  DOI：——

  日期：——