methyl 3α,12α-diacetyloxy-7α-hydroxy-5β-cholan-24-oate | 58822-33-6

• 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: methyl 3α,12α-diacetyloxy-7α-hydroxy-5β-cholan-24-oate
• 英文别名: methyl 3α,12α-diacetoxy-7α-hydroxy-5β-cholan-24-oate；methyl 3α,12α-diacetoxy-7α-hydroxy-5β-cholanate；methyl 3,12-diacetyloxycholate；methyl cholate 3,12-diacetate；3α,12α-diacetoxy-7α-hydroxy-5β-cholan-24-oic acid methyl ester；3α,12α-Diacetoxy-7α-hydroxy-5β-cholan-24-saeure-methylester；Vkamwgfhtdglcf-cxflvziosa-；methyl (4R)-4-[(3R,5R,7R,8R,9S,10S,12S,13R,14S,17R)-3,12-diacetyloxy-7-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
• CAS: 58822-33-6
• 化学式: C₂₉H₄₆O₇
• 分子量: 506.68
• InChiKey: VKAMWGFHTDGLCF-CXFLVZIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3α,12α-diacetyloxy-7α-hydroxy-5β-cholan-24-oate 在 calcium hydride 、 4 A molecular sieve 、 三氟化硼乙醚 、 四丁基碘化铵 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 37.0h， 生成 [(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-12-acetyloxy-3-[(1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]oxy-17-[(2R)-5-methoxy-5-oxopentan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-7-yl] naphthalene-2-carboxylate
  参考文献：
  名称：

  Cholic acid derived novel chiral auxiliaries for asymmetric Diels–Alder reactions

  摘要：

  胆酸基手性丙烯酸酯 5 在 BF3Â-OEt2 存在下与环戊二烯生成 DielsâAlder 加合物，非对映选择性为 88%。

  DOI：

  10.1039/c39930001469
• 作为产物：
  描述：

  (3alpha,5beta,12alpha)-3,12-双(乙酰氧基)-7-酮基胆烷-24-酸甲酯 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以83%的产率得到methyl 3α,12α-diacetyloxy-7α-hydroxy-5β-cholan-24-oate
  参考文献：
  名称：

  Cholic acid derived novel chiral auxiliaries for asymmetric Diels–Alder reactions

  摘要：

  胆酸基手性丙烯酸酯 5 在 BF3Â-OEt2 存在下与环戊二烯生成 DielsâAlder 加合物，非对映选择性为 88%。

  DOI：

  10.1039/c39930001469

文献信息

• Synthesis of disulfates of unconjugated and conjugated bile acids.
  作者：JUNICHI GOTO、YOSHIHISA SANO、TOSHIYUKI CHIKAI、TOSHIO NAMBARA

  DOI：10.1248/cpb.35.4562

  日期：——

  The disulfates of unconjugated, and glycine- and taurine-conjugated bile acids have been synthesized. Cholic acid derivatives appropriately protected were sulfated with sulfur trioxide-triethylamine complex in pyridine in the usual manner. Subsequent hydrolysis and/or sodium borohydride reduction provided the desired disulfates of cholates in satisfactory yields. Dihydroxylated bile acid disulfates were also prepared. The nuclear magnetic resonance spectral data for bile acid disulfates and related compounds are tabulated.

  已合成未结合的以及甘氨酸和牛磺酸结合的胆汁酸的二硫酸盐。适当保护的胆酸衍生物在吡啶中采用三氧化硫-三乙胺络合物进行磺酸化，方法如常。随后水解和/或氢化钠还原提供了理想的胆酸二硫酸盐，收率令人满意。同时也制备了二羟基胆汁酸的二硫酸盐。胆汁酸二硫酸盐及相关化合物的核磁共振光谱数据已列出。
• First Chemical Synthesis, Aggregation Behavior and Cholesterol Solubilization Properties of Pythocholic Acid and 16α-Hydroxycholic Acid
  作者：Nonappa、Uday Maitra

  DOI：10.1002/ejoc.200700211

  日期：2007.7

  The first chemical synthesis of pythocholic acid, a major component of python’s bile, and $3\alpha$,$7\alpha$,$12\alpha$,$16\alpha$-tetrahydroxy-$5\beta$-cholan-24-oic acid ($16\alpha$-hydroxycholic acid), a minor component in Shoebill stork’s bile, was achieved starting from readily available cholic acid in overall yields of 5% and 5.5%, respectively, through a common intermediate. A biomimetic template-directed

  蟒蛇胆汁的主要成分，毒胆酸和$3\alpha$,$7\alpha$,$12\alpha$,$16\alpha$-tetrahydroxy-$5\beta$-cholan-24-oic酸的首次化学合成（ $16\alpha$-羟基胆酸）是鹳鹳胆汁中的一个次要成分，它是从易得的胆酸开始，通过一个共同的中间体获得的，总产率分别为 5% 和 5.5%。仿生模板导向的远程功能化策略被用来选择性地功能化类固醇骨架的 C-16。该合成涉及一系列区域和化学选择性转化。Pythocholic acid 表现出异常低的临界胶束浓度 (CMC)，具有高胆固醇溶解能力。
• Bile Acid Derived<i>Tropos Vaulted</i>Bi­naphth­ylphosphites: Synthesis, Stereo­chemical Characterization and Complexation to Rhodium
  作者：Varsha R. Jumde、Anna Iuliano

  DOI：10.1002/ejoc.201300024

  日期：2013.7

  tropos ligands. The extent of the prevalence of the M sense of twist depends on the position at which the binaphthylphosphite moiety is linked on the bile acid skeleton. The three phosphites were mixed with [Rh(COD)2][BF4] and the resulting complexes were analyzed by variable temperature 31P NMR spectroscopy, thereby obtaining information on their stereochemical characteristics, which reflect the different

  从胆酸或脱氧胆酸和 1,1'-二羟基-2,2'-联萘的合适衍生物开始，合成了三种不同的 2,2'-亚磷酸联苯酯，并通过 CD 和 NMR 光谱分析了它们的立体化学特征。光谱数据清楚地证明了胆甾烷骨架诱导柔性联萘部分的 M 普遍螺旋感的能力，从而产生了原配体。M 扭曲感的流行程度取决于亚磷酸联苯酯部分在胆汁酸骨架上的连接位置。三种亚磷酸酯与 [Rh(COD)2][BF4] 混合，所得配合物通过变温 31P NMR 光谱分析，从而获得有关其立体化学特征的信息，
• Transesterification of the α-keto ester in methyl pheophorbide-a
  作者：Satoshi Shinoda、Atsuhiro Osuka

  DOI：10.1016/0040-4039(96)01075-1

  日期：1996.7

  Transesterification of the α-keto methyl ester in methyl pheophorbide-a proceeds smoothly under neutral conditions, allowing the preparation of a variety of models such as steroid-pheophorbide, pyromellitimide-pheophorbide, thymidine-pheophorbide, pheophorbide dimer, and porphyrin-pheophorbide.

  在中性条件下，α-酮甲基酯在甲基脱镁叶绿酸-a中的酯交换反应顺利进行，从而可以制备多种模型，例如甾体-脱镁叶绿酸，均苯四甲酰亚胺-脱镁叶绿酸，胸苷-脱镁叶绿酸，脱镁叶绿酸二聚体和卟啉-脱镁铝绿化。
• Goto, Junichi; Kato, Hiroaki; Kaneko, Kiyoshi, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 11, p. 3389 - 3394
  作者：Goto, Junichi、Kato, Hiroaki、Kaneko, Kiyoshi、Nambara, Toshio

  DOI：——

  日期：——