epi-androsteronyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside | 1384251-58-4

• 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: epi-androsteronyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-[[(3S,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1384251-58-4
• 化学式: C₂₉H₄₂O₇
• 分子量: 502.648
• InChiKey: YPMNYLJZIVMPBA-DHZHZGSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  表雄酮 、 乙酰化葡萄烯糖 在 triflic acid supported on silica gel 作用下， 反应 2.0h， 以84%的产率得到epi-androsteronyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside
  参考文献：
  名称：

  CF3SO3H–SiO2 as catalyst for Ferrier rearrangement: an efficient procedure for the synthesis of pseudoglycosides

  摘要：

  An efficient method for the conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated glycosides by using triflic acid on SiO2 as catalyst has been established. A series of 2,3-unsaturated glucosides were synthesized in good yield and high anomeric selectivity under transition metal-free conditions. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.019

文献信息

• Iron(III) triflate, a new efficient catalyst for Type I Ferrier Rearrangement
  作者：Peiran Chen、Shaoshan Wang

  DOI：10.1016/j.tet.2012.04.115

  日期：2012.7

  By using iron(III) triflate as catalyst, an improved method for the synthesis of 2,3-unsaturated-O-glycosides has been established. A series of 2,3-unsaturated-O-glucosides were obtained from 2,4,6-tri-O-acetyl-d-glucal in good yield and high anomeric selectivity.

  通过使用三氟甲磺酸铁（III）作为催化剂，已经建立了一种合成2,3-不饱和-O-糖苷的改进方法。一系列的2,3-unsaturated- ö从获得-glucosides -2,4,6-三ö乙酰基d -glucal以良好的收率和高的异头选择性。
• RuCl3·3H2O as catalyst for Ferrier rearrangement: an efficient procedure for the preparation of pseudoglycosides
  作者：Peiran Chen、Lei Lin

  DOI：10.1016/j.tet.2013.09.061

  日期：2013.11

  By using RuCl3 center dot 3H(2)O as catalyst, an improved method for the synthesis of 2,3-unsaturated-glycosides has been established. A series of 2, 3-unsaturated-glucosides were obtained from 2,4,6-tri-O-acetyl-D-glucal or 3,4-di-O-acetyl-6-deoxy-L-glucal in good yield and high anomeric selectivity. (C) 2013 Elsevier Ltd. All rights reserved.
• Sm(OTf)3 as a highly efficient catalyst for the synthesis of 2,3-unsaturated O- and S-pyranosides from glycals and the temperature-dependent formation of 4-O-acetyl-6-deoxy-2,3-unsaturated S-pyranosides and 4-O-acetyl-6-deoxy-3-alkylthio glycals
  作者：Peiran Chen、Dalin Zhang

  DOI：10.1016/j.tet.2014.09.060

  日期：2014.11

  By using Sm(OTf)(3) as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed. A series of 2,3-unsaturated glycosides were obtained from 3,4,6-tri-O-acetyl-D-glucal or 3,4-di-O-acetyl-L-rhamnal under mild reaction conditions in good yield and high anomeric selectivity. It was found that under certain conditions, reaction of 3,4-di-O-acetyl-L-rhamnal with thiol leads to temperature-dependent formation of C-1-S and C-3-S product. A temperature-dependent profile of the yield of these two products is given. (C) 2014 Elsevier Ltd. All rights reserved.
• An efficient procedure for the synthesis of 2,3-unsaturated-O-glycosides: TiCl3(OTf) as the catalyst for type I Ferrier rearrangement
  作者：Peiran Chen、Lei Lin

  DOI：10.1016/j.tet.2013.04.051

  日期：2013.6

  An efficient type I Ferrier rearrangement reaction system for the synthesis of 2,3-unsaturated-O-glycosides has been established by using TiCl3(OTf) as the catalyst. A series of 2,3-unsaturated-O-glucosides were prepared from 3,4,6-tri-O-acetyl-D-glucal in good yield and high anomeric selectivity. (C) 2013 Elsevier Ltd. All rights reserved.