3β,16β-diacetoxy-17α-hydroxypregn-5-en-20-one | 23357-24-6

• 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: 3β,16β-diacetoxy-17α-hydroxypregn-5-en-20-one
• 英文别名: 3β,16β-diacetoxy-17-hydroxy-pregn-5-en-20-one；3β,16β-Diacetoxy-17-hydroxy-pregn-5-en-20-on；Pregn-5-en-20-one, 3,16-bis(acetyloxy)-17-hydroxy-, (3beta,16beta)-；[(3S,8R,9S,10R,13S,14S,16S,17S)-17-acetyl-16-acetyloxy-17-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 23357-24-6
• 化学式: C₂₅H₃₆O₆
• 分子量: 432.557
• InChiKey: CDKRMWAXMJVXDE-PVGGLHBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3β,16β-diacetoxy-17α-hydroxypregn-5-en-20-one 在 sodium tetrahydroborate 作用下， 生成 3beta,16beta-Diacetoxyandrost-5-en-17-one
  参考文献：
  名称：

  Cooley et al., Journal of the Chemical Society, 1955, p. 4373,4375

  摘要：

  DOI：
• 作为产物：
  描述：

  16-脱氢孕烯醇酮乙酸酯 在 sodium hydroxide 、 硫酸 、 双氧水 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 3β,16β-diacetoxy-17α-hydroxypregn-5-en-20-one
  参考文献：
  名称：

  The first synthesis of the aglycone of the potent anti-tumor steroidal saponin OSW-1

  摘要：

  The protected aglycone (21e-beta) of the potent anti-tumor agent OSW-1 (1) was synthesized in 9 steps from 5-androsten-3 beta-ol-17-one (10) in 55% overall yield. Key reactions involve ene installation of the side chain, regio and stereoselective dihydroxylation and diastereoselective reduction of the C16 ketone. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10814-0

文献信息

• Synthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and<scp>d</scp>-homoandrostane. Tandem “click” reaction/Cu-catalyzed<scp>d</scp>-homo rearrangement
  作者：Yury N. Kotovshchikov、Gennadij V. Latyshev、Nikolay V. Lukashev、Irina P. Beletskaya

  DOI：10.1039/c4ob00404c

  日期：——

  Copper-catalyzed 1,3-dipolar cycloaddition has been employed in the reaction of steroidal azides with various terminal alkynes. A number of novel 1,2,3-triazolyl derivatives of pregnane, androstane and D-homoandrostane were obtained in high yield (70–98%). The developed synthetic protocols allowed us to attach the triazolyl moiety to both the side chain and the steroidal backbone directly, despite

  铜催化的1，3-偶极环加成已用于甾族叠氮化物与各种末端炔的反应中。以高收率（70-98％）获得了许多新型的孕烷，雄烷酮和D-高雄甾烷的1,2,3-三唑基衍生物。尽管多环系统施加了空间位阻，但发达的合成方案使我们能够将三唑基部分直接连接到侧链和甾族骨架上。Cu（II）的存在显示出在温和条件下引起D-均质重排。合理选择铜预催化剂可以使我们与串联D一起进行“点击”反应-homo重排或在没有此过程的情况下。研究了在Cu（II）催化下16-杂取代的类固醇发生D- homo重排的趋势。
• Steroid saponins and sapogenins of underground parts of Trillium kamtschaticum PALL. I. Component sapogenins and structure of pennogenin.
  作者：TOSHIHIRO NOHARA、KAZUMOTO MIYAHARA、TOSHIO KAWASAKI

  DOI：10.1248/cpb.22.1772

  日期：——

  From the rhizomes of Trillium kamtschaticum PALL. diosgenin, pennogenin (II''), kryptogenin (III), bethogenin (IV) and a new compound (XI), mp 149-151°, [α]D-192.7°, were obtained. XI was assigned the structure, 26-chloro-26-deoxykryptogenin, and thought to be an artefact formed during hydrolysis with hydrochloric acid of a glycoside of kryptogenin or a related sapogenin. Of the two formulae II (Marker, et al.) and II' (Heusler, et al.) of pennogenin, II was favored on the basis of NMR spectral and chemical evidences, and pennogenin is represented as 25D-spirost-5-ene-3β, 17α-diol (II'') having the same configurations at C-16, 17, 20, and 22 as usual steroid sapogenins.

  来自 Trillium kamtschaticum PALL 的根茎。得到薯蓣皂苷元、青皂甙元(II'')、隐皂甙元(III)、倍草皂甙元(IV)和新化合物(XI)，熔点149-151°，[α]D-192.7°。 XI 的结构为 26-氯-26-脱氧氪原，并被认为是在用盐酸水解氪原或相关皂苷元的糖苷时形成的人工产物。在pennogenin的两个式II（Marker等人）和II'（Heusler等人）中，根据NMR光谱和化学证据，II更受青睐，pennogenin表示为25D-spirost-5-ene -3β、17α-二醇(II'')在C-16、17、20和22处具有与通常的类固醇皂苷元相同的构型。
• Heussler; Wettstein, Chemische Berichte, 1954, vol. 87, p. 1301,1308
  作者：Heussler、Wettstein

  DOI：——

  日期：——
• Some Experiments with 16β-Bromo-17α-acetoxy-20-keto Steroids. Synthesis of 16α-17α-Dihydroxy-steroids and Related Compounds¹
  作者：J. ROMO、A. ROMO DE VIVAR

  DOI：10.1021/jo01114a022

  日期：1956.8
• Achrem et al., Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1969, p. 2792,2798;engl.Ausg.S.2620,2623
  作者：Achrem et al.

  DOI：——

  日期：——