[(2R,3S,6S)-6-[[(8R,9S,10R,13S,14S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3-acetyloxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate | 1432744-67-6

• 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: [(2R,3S,6S)-6-[[(8R,9S,10R,13S,14S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3-acetyloxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1432744-67-6
• 化学式: C₃₁H₄₂O₇
• 分子量: 526.67
• InChiKey: RQSIOHWNSUVKFV-ITXDKUCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  16-dehydropregnenolone 、 乙酰化葡萄烯糖 在 trichloro(trifluoromethanesulfonato)titanium(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 以72%的产率得到[(2R,3S,6S)-6-[[(8R,9S,10R,13S,14S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3-acetyloxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
  参考文献：
  名称：

  An efficient procedure for the synthesis of 2,3-unsaturated-O-glycosides: TiCl3(OTf) as the catalyst for type I Ferrier rearrangement

  摘要：

  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.

  DOI：

  10.1016/j.tet.2013.04.051