3α,6α-ditetrahydropyranyloxy-5β-cholan-24-al | 84371-41-5

• 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: 3α,6α-ditetrahydropyranyloxy-5β-cholan-24-al
• 英文别名: 3α, 6α-bis(2-tetrahydropyranyloxy)-5β-cholane-24-al；(4R)-4-[(3R,5R,6S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3,6-bis(oxan-2-yloxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanal
• CAS: 84371-41-5
• 化学式: C₃₄H₅₆O₅
• 分子量: 544.816
• InChiKey: HMEIETYWMZNJIC-DCZVKRHRSA-N

物化性质

• 熔点：
  92-94 °C
• 沸点：
  624.3±55.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3α,6α-ditetrahydropyranyloxy-5β-cholan-24-al 在 盐酸 、 Ru(OAc)2((S)-BINAP) 、 potassium tert-butylate 、 氢气 、 对甲苯磺酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 20.0~60.0 ℃ 、202.66 kPa 条件下， 反应 56.0h， 生成
  参考文献：
  名称：

  Divergent and stereoselective synthesis of dafachronic acids

  摘要：

  A new divergent synthesis of DAF-12 ligands, namely Delta(4)- and Delta(7)-dafachronic acid, is described starting from the natural bile acid hyodeoxycholic acid. Homologation of the side chain followed by stereoselective reduction of the Delta(24) olefinic linkage, 6 alpha-dehydroxylation and C-3-oxidation affords dafachronic acids in good yields and high diastereoselectivity making this approach easily accessible and scalable. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.022
• 作为产物：
  描述：

  3α,6α-ditetrahydropyranyloxy-5β-cholan-24-oic acid 在 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 3α,6α-ditetrahydropyranyloxy-5β-cholan-24-al
  参考文献：
  名称：

  Divergent and stereoselective synthesis of dafachronic acids

  摘要：

  A new divergent synthesis of DAF-12 ligands, namely Delta(4)- and Delta(7)-dafachronic acid, is described starting from the natural bile acid hyodeoxycholic acid. Homologation of the side chain followed by stereoselective reduction of the Delta(24) olefinic linkage, 6 alpha-dehydroxylation and C-3-oxidation affords dafachronic acids in good yields and high diastereoselectivity making this approach easily accessible and scalable. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.022

文献信息

• Synthesis of 24,25-dihydroxycholesterol
  申请人：——

  公开号：US04351767A1

  公开（公告）日：1982-09-28

  This invention relates to the synthesis of steroids which are useful for their biological activity or which may be converted to steroids which have such activity. More particularly, the invention pertains to the synthesis of 24,25-dihydroxycholesterol. It includes intermediate sterols of this synthesis and processes for their preparation.

  本发明涉及合成类固醇，这些类固醇对于其生物活性有用，或者可以转化为具有这种活性的类固醇。 更具体地说，本发明涉及合成24,25-二羟基胆固醇。它包括该合成的中间类固醇以及它们的制备过程。
• US4351767A
  申请人：——

  公开号：US4351767A

  公开（公告）日：1982-09-28
• Divergent and stereoselective synthesis of dafachronic acids
  作者：Antimo Gioiello、Paola Sabbatini、Emiliano Rosatelli、Antonio Macchiarulo、Roberto Pellicciari

  DOI：10.1016/j.tet.2011.01.022

  日期：2011.3

  A new divergent synthesis of DAF-12 ligands, namely Delta(4)- and Delta(7)-dafachronic acid, is described starting from the natural bile acid hyodeoxycholic acid. Homologation of the side chain followed by stereoselective reduction of the Delta(24) olefinic linkage, 6 alpha-dehydroxylation and C-3-oxidation affords dafachronic acids in good yields and high diastereoselectivity making this approach easily accessible and scalable. (C) 2011 Elsevier Ltd. All rights reserved.