methyl 3β-formate-12α-hydroxycholanate | 42921-39-1

• 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 3β-formate-12α-hydroxycholanate
• 英文别名: (Methyl-3β.12α-dihydroxy-cholanat)-3-format；(Methyl-3-β.12α-dihydroxycholanat)-3β-formiat；(3β,5β,12α)-3-formyloxy-12-hydroxycholan-24-oic acid methyl ester；methyl (4R)-4-[(3S,5R,8R,9S,10S,12S,13R,14S,17R)-3-formyloxy-12-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: 42921-39-1
• 化学式: C₂₆H₄₂O₅
• 分子量: 434.616
• InChiKey: UKCCVKQBDLYWPC-AKQBICQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3β-formate-12α-hydroxycholanate 在 镍 chromium(VI) oxide 、 硫酸 、 氢气 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 5β-Pregnan-3,12,20-trion
  参考文献：
  名称：

  Neue beiträge zur biogenese der cardenolide in digitalis lanata

  摘要：

  摘要 5βH-pregnane-3β-ol-20-one 和 5βH-pregnane-3,20-dione 给予洋地黄植物后可相互转化，形成洋地黄毒苷、洋地黄毒苷和吉托昔明。5αH-pregnane-3β-ol-20-one 没有产生 uzarigenin。5βH-Δ 14 -pregnene-3β-ol-20-one 不是洋地黄毒苷的前体，而 5β,14βH-pregnane-3β-ol-20-one 是，但程度很小。5βH-孕烷-3β,12β-diol-20-one 以良好的产率转化为洋地黄毒苷，就像洋地黄毒苷。

  DOI：

  10.1016/s0031-9422(00)85268-1
• 作为产物：
  描述：

  去氧胆酸 在 吡啶 、 对甲苯磺酸 作用下， 反应 72.0h， 生成 methyl 3β-formate-12α-hydroxycholanate
  参考文献：
  名称：

  Crystal structure of 3β,12α-dihydroxy-5β-cholan-24-oic acid (iso-deoxycholic acid)

  摘要：

  Iso-deoxycholic acid (3 beta,12 alpha-dihydroxy-5 beta-cholan-24-oic acid, iso-DCA), the 3 beta hydroxy epimer of deoxycholic acid (DCA), was synthesized from deoxycholic acid. The crystals, obtained by recrystallization from p-xylene, are orthorhombic, space group P2(1)2(1)2(1), with a = 7.3232(6), b = 10.5938(16) and c = 28.2957(18) Angstrom. The crystals contained no inclusion molecules, and thus differed from those of DCA when recrystallized from o-, m- and p-xylene. This absence of solvate molecules could explain the reduction of approximate to 3 Angstrom in the b-axis length in iso-DCA when compared with that of DCA with xylene guests. (C) 2000 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(99)00410-x

文献信息

• Blood pool agents for nuclear magnetic resonance diagnostics
  申请人：Bracco Imaging S.p.A.

  公开号：EP1935435B1

  公开（公告）日：2017-09-06
• 3β, 12β-Dihydroxycholanic Acid^*
  作者：Frederic C. Chang、Neville F. Wood、William G. Holton

  DOI：10.1021/jo01017a004

  日期：1965.6
• Scale-Up of Trisodium [(3β,5β,12α)-3-[[4(<i>S</i>)-4-[Bis[2-[bis[(carboxy-<i>kO</i>)methyl]amino-<i>kN</i>]ethyl]amino-<i>kN</i>]-4-(carboxy-<i>kO</i>)-1-oxobutyl]amino]-12-hydroxycholan-24-oato(6-)]gadolinate(3-)], a Gd(III) Complex under Development As a Contrast Agent for MRI Coronary Angiography
  作者：Pier Lucio Anelli、Marino Brocchetta、Luciano Lattuada、Giuseppe Manfredi、Pierfrancesco Morosini、Marcella Murru、Daniela Palano、Marco Sipioni、Massimo Visigalli

  DOI：10.1021/op900008a

  日期：2009.7.17

  Process chemistry involved in the discovery and development routes to trisodium [(3 beta,5 beta,12(alpha)-3-[[4(S)-4-[bis[2-[bis[(carboxy-kO)methyl]amino-kN]ethyl]amino-kN]4-(carboxy-kO)-1-oxobutyl]- amino]-12-hydroxycholan-24-oato(6-)]gadolinate(3-)] (B22956/1) starting from L-glutamic acid and (3 alpha,5 beta,12 alpha)-3,12-dihydroxycholan-24-oic acid is described. The best process is based on seven chemical steps and overcomes difficult purification protocols. Such process has been successfully implemented to prepare multikilogram batches of the target compound in 20% overall yield from (3 alpha,5 beta,12 alpha)-3,12-dihydroxycholan-24-oic acid.
• BLOOD POOL AGENTS FOR NUCLEAR MAGNETIC RESONANCE DIAGNOSTICS
  申请人：BRACCO IMAGING S.p.A.

  公开号：EP1140209B1

  公开（公告）日：2008-08-20