5α,6β-dihydroxy-5α-cholest-7-en-3β-yl acetate | 2551-04-4

• 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: 5α,6β-dihydroxy-5α-cholest-7-en-3β-yl acetate
• 英文别名: 5,6β-dihydroxy-5α-cholest-7-en-3β-yl acetate；5α-cholest-7-ene-3β,5,6β-triol 3-acetate；cholest-7-ene-3β,5α,6β-triol 3-acetate；Cholest-7-en-3β,5α,6β-triol-3-acetat；[(3S,5R,6R,9S,10R,13R,14R,17R)-5,6-dihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 2551-04-4
• 化学式: C₂₉H₄₈O₄
• 分子量: 460.698
• InChiKey: SOIFUSGRQKSILZ-LTLZNLBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5α,6β-dihydroxy-5α-cholest-7-en-3β-yl acetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 cholest-7-en-3β,5α,6β-triol
  参考文献：
  名称：

  Pyridine-idnduced dishielding of 4-methylene protons for the determination of C-6 stereochemistry of sterols having a 5.ALPHA.,6-diol moiety. Revision of the C-6 stereochemistry of marine sterol isolated from a sponge, Dysidea sp.

  摘要：

  通过吡啶诱导去屏蔽的质子核磁共振方法，展示了在具有5α, 6β-二醇基团的甾醇C-6位的立体化学分配中的应用。因此，像胆甾-7-烯-3β, 5α, 6α-三醇（8）这样的6α-异构体的4α-氢共振在大约3.0 ppm处被观察到，而像胆甾-7-烯-3β, 5α, 6β-三醇（10）这样的6β-异构体的4β-氢共振同样在大约3.0 ppm处被观察到。该方法被应用于从海绵Dysidea sp.分离出的海洋甾醇（4），并得出结论，结构应修订为6α-异构体（5），而非报告的6β-异构体（4）。

  DOI：

  10.1248/cpb.33.3129
• 作为产物：
  描述：

  7-脱氢醋酸胆固醇 在 双氧水 、 甲基三氧化铼(VII) 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以52%的产率得到5α,6β-dihydroxy-5α-cholest-7-en-3β-yl acetate
  参考文献：
  名称：

  Lasalvia, Maria; Musumeci, Domenica; Piccialli, Vincenzo, Journal of Chemical Research, Miniprint, 1998, # 11, p. 2988 - 2995

  摘要：

  DOI：

文献信息

• Zur Chemie des Ecdysons, V: Versuche zur Darstellung von Steroid‐Δ ⁷ ‐6‐ketonen mit 3.4‐Diol‐Gruppierung
  作者：Clemens Rufer、Hans Hoffmeister、Hans Schairer、Martin Traut

  DOI：10.1002/cber.19650980742

  日期：1965.7

  entsprechende Dien-(5.7)-diol-(3β.4β) war nicht erhältlich; aus 7α-Brom- bzw. 7-Hydroxy-cholesten-(5)-diol-(3β.4β)-Derivaten ließ sich kein Halogenwasserstoff bzw. Wasser abspalten. Cholestan-diol-(3β.4β)-on-(6)-diacetat wurde synthetisiert.

  类固醇Δ温和合成路线7通过Δ-6-酮引线5.7 -dienes。可以代表胆甾醇-（5.7）-二醇-（3β.4α）-二乙酸酯。相应的二烯-（5.7）-二醇-（3β.4β）不可用；不能从7α-溴-或7-羟基胆固醇-（5）-二醇-（3β.4β）衍生物中分离出卤化氢或水。合成了胆甾醇-二醇-（3β.4β）-一-（6）-二乙酸酯。
• CH3ReO3-catalyzed oxidation of cholesta-5,7-dien-3β-yl acetate with the urea-hydrogen peroxide adduct under various conditions. Synthesis of the natural epoxy sterol 9α,11α-epoxy-5α-cholest-7-en-3β,5,6β-triol
  作者：Domenica Musumeci、Donato Sica

  DOI：10.1016/s0039-128x(02)00017-x

  日期：2002.6

  oxidation of cholesta-5,7-dien-3β-yl acetate (4) with the urea-hydrogen peroxide adduct (UHP) using methyltrioxorhenium (MTO) as catalyst, under various conditions. Specifically, the effects of using different solvents (CHCl3 and ethers) and additives (EtOH and pyridine) on the course of the MTO-catalyzed oxidation of 4 were investigated. Some new steroids (6, 9, 10 and 11), obtained from this oxidation

  摘要 本文描述了使用甲基三氧铼 (MTO) 作为催化剂，在各种条件下，用尿素-过氧化氢加合物 (UHP) 氧化 cholesta-5,7-dien-3β-yl acetate (4)。具体而言，研究了使用不同溶剂（CHCl3 和醚）和添加剂（乙醇和吡啶）对 MTO 催化氧化 4 过程的影响。根据化学证据和光谱数据的解释，包括 HH COZY 和 HMBC 实验，从这种氧化中获得的一些新的类固醇（6、9、10 和 11）被分离和表征。MTO/UHP氧化体系氧化4的最佳溶剂是乙醚。在该溶剂中，反应是干净的并且得到作为主要产物的乙酸 5,6β-dihydroxy-5α-cholest-7-en-3β-yl (8, 65% 产率)，以比文献报道的更简单的程序和更高的产率获得。Sterol 8 是合成许多海洋来源的类固醇的关键中间体化合物，具有生物活性，在 B/C 环处氧化。事实上，从二醇 8 开始，我们进行了天然细胞毒性环氧甾醇
• Structure Elucidation of Oxygenated Sterols from Eggs of Sea Hare,<i>Aplysia Juliana</i>
  作者：Yoshihiro Yamaguchi、Yukio Nakanishi、Teruyuki Shimokawa、Shigeru Hashiguchi、Akira Hayashi

  DOI：10.1246/cl.1992.1713

  日期：1992.9

  Cholest-7-en-6R-methoxy-3S,5R-diol, a new sterol, and cholest-7-en-3S,5R,6R-triol were isolated from eggs of sea hare, Aplysia Juliana, and their structures and absolute configurations deduced by spectroscopic studies and chemical synthesis.

  从海兔Aplysia Juliana的卵中分离得到胆甾醇7-en-6R-甲氧基-3S,5R-二醇新甾醇和cholest-7-en-3S,5R,6R-三醇及其结构和绝对值通过光谱研究和化学合成推导出的构型。
• Studies towards the synthesis of polyoxygenated steroids. Reaction of 7,9(11)-diene steroids with RuO4.
  作者：Giacomo Notaro、Vincenzo Piccialli、Donato Sica、Dina Smaldone

  DOI：10.1016/s0040-4020(01)85020-1

  日期：1994.4

  In order to find an entry to C-ring oxygenated steroids, the reaction of ruthenium tetroxide with some Delta(7,9(11))-sterols gas been explored. The reaction has been performed both at -70 degrees C and room temperature using an equimolecular amount of the oxidant and acetone-water as solvent system in the absence of a cooxidant. The change in the temperature conditions moderately affects the yields of the reaction products. When 3 beta,6 alpha- and 3 beta,6 beta-diacetoxy-Delta(7,9(11))-sterols were used the diene system was predominantly attacked at the 9(11)-double bond from the alpha-face of the molecule giving Delta(7)-9 alpha-hydroxy-11-keto- and Delta(7)-9 alpha,11 alpha-dihydroxy-sterols. RuO4 oxidation of cholesta-7,9(11)-dien-3 beta-yl acetate, yielded, in addition to the above oxidation products, minor amounts of three related C-7,C-11 oxigenated 8 alpha,9 alpha-epoxysterols, arising from the oxidation of both double bonds of the diene system. These results, that in part parallel those we recently found on RuO4 oxidation of trisubstituted [Delta(4), Delta(5) and Delta(7)] steroidal alkenes, shed further light on the reactivity of this oxidizing agent which, neverthless, seems far from being completely understood. In addition, our procedure furnishes a reliable route to Delta(7)-9 alpha,11 beta-dihydroxysterols via LiAlH4 reduction of the 11-keto group.
• Pyridine-idnduced dishielding of 4-methylene protons for the determination of C-6 stereochemistry of sterols having a 5.ALPHA.,6-diol moiety. Revision of the C-6 stereochemistry of marine sterol isolated from a sponge, Dysidea sp.
  作者：YOSHINORI FUJIMOTO、TAKETOSHI YAMADA、NOBUO IKEKAWA

  DOI：10.1248/cpb.33.3129

  日期：——

  The utility of the proton nuclear magnetic resonance method involving pyridine-induced deshielding was demonstrated for stereochemical assignment at the C-6 position of sterols having a 5α, 6ζ-diol moiety. Thus, the 4α-hydrogen resonance of 6α-isomers such as cholest-7-ene-3β, 5α, 6α-triol (8) is observed at ca. 3.0 ppm, whereas the 4β-hydrogen resonance of 6β-isomers such as cholest-7-ene-3β, 5α, 6β-triol (10) is observed at ca. 3.0 ppm. This method was applied to a marine sterol (4) isolated from a sponge, Dysidea sp., and it was concluded that the structure should be revised to the 6α-isomer (5) rather than the reported 6β-isomer (4).

  通过吡啶诱导去屏蔽的质子核磁共振方法，展示了在具有5α, 6β-二醇基团的甾醇C-6位的立体化学分配中的应用。因此，像胆甾-7-烯-3β, 5α, 6α-三醇（8）这样的6α-异构体的4α-氢共振在大约3.0 ppm处被观察到，而像胆甾-7-烯-3β, 5α, 6β-三醇（10）这样的6β-异构体的4β-氢共振同样在大约3.0 ppm处被观察到。该方法被应用于从海绵Dysidea sp.分离出的海洋甾醇（4），并得出结论，结构应修订为6α-异构体（5），而非报告的6β-异构体（4）。