5β-pregnane-3α,17α,20β,21-tetraol | 3615-89-2

• 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: 5β-pregnane-3α,17α,20β,21-tetraol
• 英文别名: (3R,5R,8R,9S,10S,13S,14S,17R)-17-[(1S)-1,2-dihydroxyethyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 3615-89-2
• 化学式: C₂₁H₃₆O₄
• 分子量: 352.514
• InChiKey: MQSSTQLJJOVNQF-YAWPOEEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5β-pregnane-3α,17α,20β,21-tetraol 以 二乙二醇 为溶剂， 生成 21-Brom-5β-pregnan-3α,17,20βF-triol
  参考文献：
  名称：

  四对侧链环氧异构体在20位碳上的合成，这些分子衍生自5-beta-pregnan-3-alpha-ol。

  摘要：

  DOI：

  10.1021/jo01269a001
• 作为产物：
  描述：

  (3R,5R,8R,9S,10S,13S,14S,17R)-10,13-Dimethyl-17-(R)-oxiranyl-hexadecahydro-cyclopenta[a]phenanthrene-3,17-diol 在 硫酸 作用下， 生成 5β-pregnane-3α,17α,20β,21-tetraol
  参考文献：
  名称：

  四对侧链环氧异构体在20位碳上的合成，这些分子衍生自5-beta-pregnan-3-alpha-ol。

  摘要：

  DOI：

  10.1021/jo01269a001

文献信息

• Diethylhydrogensilyl cyclic diethylsilylene derivatives in gas chromatography-mass spectrometry of hydroxylated steroids. II. Pregnanes with a hydroxylated 17.BETA.-side-chain.
  作者：MASATAKA ISHIBASHI、MASAHIRO ITOH、KOUWA YAMASHITA、HIROSHI MIYAZAKI、HISAO NAKATA

  DOI：10.1248/cpb.34.3298

  日期：——

  The gas chromatographic-mass spectrometric properties of diethylhydrogensilyl cyclic diethylsilylene derivatives of hydroxypregnanes were studied. Pregnanes with a sterically hindered 11β-hydroxyl group were smoothly silylated with a new silylating agent, N, O-bis(diethylhydrogensilyl)-trifluoroacetamide, under mild conditions. The mass spectra of these derivatives were characterized by the appearance of the intense molecular ion peak, which provides convenient and reliable confirmation of the molecular weight of these hydroxypregnanes. The most characteristic fragment ions were those at m/z 185 for 17, 20-diols and at m/z 287 for 17, 20, 21-triols, which were produced by cleavage at the C(13)-C(17) and C(15)-C(16) bonds with hydrogen atom transfer. This indicates that all of the major fragmentations are directed by the cyclic diethylsilylene group. Another fragmentation common to the spectra was the successive loss of diethylhydrogensilanol from the molecular ion. A remarkable difference in the appearance of peaks was observed between DEHS-DES derivatives of a 17α, 20α, 21-triol and its 20β-isomer. Structures are proposed for some of these fragment ions.

  研究了羟基孕烷的二乙基氢硅烷基环二乙基硅烷衍生物的气相色谱-质谱特性。在温和的条件下，用一种新的硅烷化剂 N, O-双（二乙基氢代苯甲酰）-三氟乙酰胺顺利地硅烷化了带有立体受阻的 11β- 羟基的孕烷。这些衍生物的质谱特征是出现了强烈的分子离子峰，这为确定这些羟基孕烷的分子量提供了方便可靠的依据。最有特征的碎片离子是 17、20-二醇的 m/z 185 和 17、20、21-三醇的 m/z 287，它们是通过氢原子转移裂解 C(13)-C(17) 和 C(15)-C(16) 键产生的。这表明所有主要碎片都是由环状二乙基硅基引导的。光谱中的另一个共同碎片是分子离子中的二乙基氢硅醇相继消失。在 17α、20α、21-三醇的 DEHS-DES 衍生物与其 20β 异构体之间，观察到峰值出现的明显差异。提出了其中一些碎片离子的结构。
• Diethylhydrogensilyl cyclic diethylsilylene derivatives in gas chromatography/mass spectrometry of hydroxylated steroids. III-Fragmentations of 5β-pregnane-17,20,21-triol derivatives
  作者：Hisao Nakatat、Masataka Ishibashi、Masahiro Itoh、Hiroshi Miyazaki

  DOI：10.1002/oms.1210220107

  日期：1987.1

  AbstractA reaction of N,O‐bis‐(diethylhydrogensilyl) trifluoroacetamide with 5β‐pregnane‐17,20,21‐triols afforded diethylhydrogensilyl (DEHS) cyclic diethylsilylene (DES) derivatives. 5β‐Pregnane‐3α,17α,20β,21‐tetraol yielded the 3α,21‐bis‐DEHS‐17α,20β‐DES compound, whereas the structure of the major product from its 20α isomer was assigned as the 3α,17α‐bis‐DEHS‐20α,21‐DES derivative, which would undergo facile isomerization to the unstable 3α,21‐bis‐DEHS‐17α,20α‐DES structure under electron ionization. Fragmentations of these DEHS‐DES compounds are discussed on the basis of isotope labelling experiments, linked scanning data, and accurate mass measurements.
• METHODS, COMPOSITIONS, AND KITS FOR THE TREATMENT OF CANCER
  申请人：Haggerty Timothy J.

  公开号：US20140335050A1

  公开（公告）日：2014-11-13

  The invention features methods, compositions, and kits for the administration of an HSP90 inhibitor, OBAA, flunarizine, aphidicolin, damnacanthal, dantrolene, or an analog thereof, alone, or in combination with, e.g., a TAA, an antigen-binding scaffold (e.g., an antibody, a soluble T cell receptor, or a chimeric receptor) specific for a TAA, a cell (e.g., a white blood cell that targets a cancer cell), and/or an IFN-β receptor agonist or an IFN-γ receptor agonist, for the treatment of cancer.