(R)-1-(benzyloxy)-3-((triethylsilyl)oxy)propan-2-ol | 1373441-10-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1-(benzyloxy)-3-((triethylsilyl)oxy)propan-2-ol
• 英文别名: (2R)-1-phenylmethoxy-3-triethylsilyloxypropan-2-ol
• CAS: 1373441-10-1
• 化学式: C₁₆H₂₈O₃Si
• 分子量: 296.482
• InChiKey: OJHFYPCXKPXUPZ-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三乙基氯硅烷 、 3-苄氧基-1,2-丙二醇 在 (4S)-4-异丙基-2-甲氧基-3-((R)-2-甲基-1-(1-甲基-1H-咪唑-2-基)丙基)恶唑烷 、 N,N-二异丙基乙胺盐酸盐 、 N,N-二异丙基乙胺 作用下， 以 叔丁醇 为溶剂， 反应 1.25h， 以40%的产率得到(R)-1-(benzyloxy)-3-((triethylsilyl)oxy)propan-2-ol
  参考文献：
  名称：

  Resolution of Terminal 1,2-Diols via Silyl Transfer

  摘要：

  Through kinetic analysis and optimization, we report an improved resolution of terminal 1,2-diols via asymmetric silyl transfer. Because the reaction is a regiodivergent resolution, the monoprotected product could be isolated in excess of 95:5 er and 40% yield. The described method offers a means of chemically differentiating a terminal 1,2-diol with concomitant resolution of the enantiomers.

  DOI：

  10.1021/jo4012909

文献信息

• Site-Selective Catalysis: Toward a Regiodivergent Resolution of 1,2-Diols
  作者：Amanda D. Worthy、Xixi Sun、Kian L. Tan

  DOI：10.1021/ja3027086

  日期：2012.5.2

  This paper demonstrates that the secondary hydroxyl can be functionalized in preference to the primary hydroxyl of a 1,2-diol. The site selectivity is achieved by using an enantioselective organic catalyst that is able to bond to the diol reversibly and covalently. The reaction has been parlayed into a divergent kinetic resolution on a racemic mixture, providing access to highly enantioenriched secondary-protected 1,2-diols in a single synthetic step.