methyl 3α,6α-ditosyloxy-25(S)-methyl-24-bishomo-5β-cholan-26-oate | 1278580-81-6

• 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,6α-ditosyloxy-25(S)-methyl-24-bishomo-5β-cholan-26-oate
• 英文别名: methyl (2S,6R)-6-[(3R,5R,6S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3,6-bis-(4-methylphenyl)sulfonyloxy-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptanoate
• CAS: 1278580-81-6
• 化学式: C₄₂H₆₀O₈S₂
• 分子量: 757.066
• InChiKey: ULAAUPNLFOJYDH-SVWCHEGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  52
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3α,6α-ditosyloxy-25(S)-methyl-24-bishomo-5β-cholan-26-oate 在 水 、 potassium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以62%的产率得到methyl 3β-hydroxy-25(S)-methyl-24-bishomochol-5-en-26-oate
  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 吡啶 、 盐酸 、 sodium tetrahydroborate 、 草酰氯 、 Ru(OAc)2((S)-BINAP) 、 potassium tert-butylate 、 氢气 、 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 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 109.0h， 生成 methyl 3α,6α-ditosyloxy-25(S)-methyl-24-bishomo-5β-cholan-26-oate
  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

• 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.