3α,6α-ditetrahydropyranyloxy-24-hydroxy-5β-cholane | 75860-96-7

• 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: 3α,6α-ditetrahydropyranyloxy-24-hydroxy-5β-cholane
• 英文别名: 3α,6α-Di(2-tetrahydropyranyloxy)-24-hydroxy-5βcholane；(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]pentan-1-ol
• CAS: 75860-96-7
• 化学式: C₃₄H₅₈O₅
• 分子量: 546.832
• InChiKey: KYQJMBFCXVGUHU-DCZVKRHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3α,6α-ditetrahydropyranyloxy-24-hydroxy-5β-cholane 在 盐酸 、 草酰氯 、 Ru(OAc)2((S)-BINAP) 、 potassium tert-butylate 、 氢气 、 二甲基亚砜 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， -50.0~60.0 ℃ 、202.66 kPa 条件下， 反应 56.0h， 生成 3α,6α-dihydroxy-25(S)-methyl-24-bishomo-5β-cholan-26-oic acid
  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 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 3α,6α-ditetrahydropyranyloxy-24-hydroxy-5β-cholane
  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

• 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.