3β-acetoxy-16β-hydroxy-5β-bisnorcholanoic acid 22->16 lactone | 359416-36-7

• 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-acetoxy-16β-hydroxy-5β-bisnorcholanoic acid 22->16 lactone
• 英文别名: 3β-acetoxy-16-hydroxy-5β-bisnorcholanic acid-(22->16) lactone；3β-acetoxy-16-hydroxy-5β-dinorcholanic acid-(22->16) lactone；(20S)-3β-acetoxy-5β-pregnane-20,16β-carbolactone；(20S)-3β-acetoxy-5β-pregnan-20,16β-carbolactone；3β-acetoxy-16β-hydroxy-23,24-dinor-5β-cholan-22-oic acid-lactone；3β-Acetoxy-16β-hydroxy-23,24-dinor-5β-cholan-22-saeure-lacton；[(1R,2S,4S,7S,8R,9S,12S,13S,16S,18R)-7,9,13-trimethyl-6-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosan-16-yl] acetate
• CAS: 359416-36-7
• 化学式: C₂₄H₃₆O₄
• 分子量: 388.547
• InChiKey: HUESGZPZXJYYMK-CIKLOOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-16β-hydroxy-5β-bisnorcholanoic acid 22->16 lactone 在 chromium(VI) oxide 、 氢氧化钾 、 溶剂黄146 作用下， 生成 sarsasapogenone lactone
  参考文献：
  名称：

  89.皂苷元。第二部分Sarsasapogenin和smilagenin

  摘要：

  DOI：

  10.1039/jr9370000414
• 作为产物：
  描述：

  [(1R,2S,4S,6S,7S,8R,9S,12S,13S,16S,18R)-6-hydroxy-7,9,13-trimethyl-6-[(2S,4S)-4-methyloxolan-2-yl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosan-16-yl] acetate 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 3β-acetoxy-16β-hydroxy-5β-bisnorcholanoic acid 22->16 lactone
  参考文献：
  名称：

  辅助溶剂分解23-螺乙炔基溴化物和甲苯磺酸酯。螺旋烷的新重排至双呋喃系统。

  摘要：

  在多种条件下，通过涉及缩醛氧原子与邻位基团参与的核糖核酸离开C23的机制，在C23处带有良好离去基团的甾体类皂甙元经历了完全立体定向的重排。赤道的（23S）-23-溴-或（23S）-23-甲苯磺酰螺甾烷与α（25R）或β（25S）定向的25-甲基的反应导致双呋喃产物的C23构型反转。起始化合物与C23处的轴向取代基（23R）的反应需要严格的条件，并导致形成伴随重排产物的相应烯烃（仅在25S异构体的情况下）。

  DOI：

  10.1021/jo020231j

文献信息

• BF3·Et2O-induced stereoselective aldol reaction with benzaldehyde, and steroid sapogenins and its application to a convenient synthesis of dinorcholanic lactones
  作者：Karen M. Ruíz-Pérez、Margarita Romero-Ávila、Verónica Tinajero-Delgado、Marcos Flores-Álamo、Martín A. Iglesias-Arteaga

  DOI：10.1016/j.steroids.2012.02.016

  日期：2012.6

  Treatment of steroid sapogenins with benzaldehyde and BF(3)·Et(2)O cleanly produces E-23(23')-benzylidenspirostanes in good yields in a reaction pathway which consists on an aldol reaction followed by a dehydration step. The obtained E-23(23')-benzylidenspirostanes can be easily converted to dinorcholanic lactones by treatment with CrO(3) in acetic acid. The synthetic sequence to dinorcholanic lactones

  用苯甲醛和 BF(3)·Et(2)O 处理类固醇皂苷元，在反应途径中以良好的收率干净地产生 E-23(23')-benzylidenspirostanes，该反应途径由醛醇反应和脱水步骤组成。获得的 E-23(23')-benzylidenspirostanes 可以很容易地通过在乙酸中用 CrO(3) 处理转化为 dinorcholanic 内酯。二降胆甾醇内酯的合成顺序与类固醇骨架中双键和羰基的存在相容。
• The unexpected course of the reaction of steroid sapogenins with diacetoxyiodobenzene and BF3·Et2O in formic acid
  作者：Martín A. Iglesias-Arteaga、Rafael O. Arcos-Ramos、José M. Méndez-Stivalet

  DOI：10.1016/j.tetlet.2007.08.071

  日期：2007.10

  The reaction of steroid sapogenins of both the 25R and 25S series with diacetoxyiodobenzene and BF3·Et2O in formic acid produced a mixture of an equatorial 23-formyloxysapogenin, a 16β,23:23,26-diepoxy-22-one and a bisnorcholanic lactone. The outcome of this reaction, that drastically differs from the same reaction in acetic acid, opens up new possibilities for the transformation of the side chain

  25 R和25 S系列甾体皂甙元与二乙酰氧基碘苯和BF 3 ·Et 2 O在甲酸中的反应产生了赤道23-甲酰氧基皂甙元的混合物，即16β，23：23,26-双环氧-22-和双降胆固醇内酯。该反应的结果与乙酸中的同一反应完全不同，为类固醇皂苷元侧链的转化开辟了新的可能性。
• Novel transformation of 23-bromosapogenins. Synthesis of (22S,23R)-22-hydroxy-23,26-epoxyfurostanes
  作者：Jacek W Morzycki、Izabella Jastrzębska

  DOI：10.1016/s0040-4039(01)01165-0

  日期：2001.8

  (22S,23S)-23-Bromosapogenins undergo rearrangement to the (22S,23R)-22-hydroxy-23,26-epoxyfurostanes during alkaline hydrolysis. An efficient degradation procedure of sarsapogenin via the corresponding bisfuran to the C(22) lactone is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  （22S,23S）-23-溴野马沸苷在碱性水解过程中发生重排，生成（22S,23R）-22-羟基-23,26-环氧化呋甾烷。文中描述了一种通过相应双呋喃将萨斯波苷素高效降解为C（22）内酯的程序。（C）2001 Elsevier Science Ltd. 保留所有权利。
• Sterols. LXXXVII. Cholesterol and Sitosterol Derivatives
  作者：Russell E. Marker、Ewald Rohrmann

  DOI：10.1021/ja01860a016

  日期：1940.3
• Deacylation reactions of 20-acetyl dinorcholanic lactones and 20,23-diacetyl furost-22-enes
  作者：Ma. Guadalupe Hernández-Linares、Jesús Sandoval-Ramírez、Socorro Meza-Reyes、Sara Montiel-Smith、María A. Fernández-Herrera、Sylvain Bernès

  DOI：10.1016/j.steroids.2009.12.008

  日期：2010.3

  We report the deacylation of (20R)-20-acetyl-23,24-dinorcholanic lactones by hydrazine hydrate, under microwave irradiation in high yields. The elimination of the 20-acetyl group proceeded with retention of configuration which contrast with other proved deacylation methods that yield a mixture of diastereoisomers. In this way, unnatural (20R)-23,24-dinorcholanic lactones can be produced rapidly on a large scale. Both (20R)- and (20S)-lactones were prepared starting from diosgenin, hecogenin and sarsasapogenin, in 72-80% overall yields. (C) 2009 Elsevier Inc. All rights reserved.