(R)-1-((triethylsilyl)oxy)propan-2-ol | 1373441-08-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-1-((triethylsilyl)oxy)propan-2-ol
• 英文别名: (2R)-1-triethylsilyloxypropan-2-ol
• CAS: 1373441-08-7
• 化学式: C₉H₂₂O₂Si
• 分子量: 190.358
• InChiKey: XEPWKKZGCCPUGH-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 、 (R)-1-((triethylsilyl)oxy)propan-2-ol 在 三苯基膦 、 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.33h， 以49%的产率得到1-((triethylsilyl)oxy)-(2R)-2-propyl 3′,4′,6′-tri-O-benzyl-2′-deoxy-2′-iodo-α-D-glucopyranoside
  参考文献：
  名称：

  Glycosylations of Glycals using N-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo- and 2-Deoxyglycosides

  摘要：

  The glycosylations of glycals and alcohols using N-iodosuccinimide (NIS) and a catalytic amount of PPh3 effectively proceeded under mild conditions to provide the corresponding 2-deoxy-2-iodoglycosides in high yields. The reactivity of the iodoglycosylations with PPh3 significantly increased in comparison to that using NIS alone as an activator. In addition, the glycosylations of glycals and alcohols using catalytic amounts of NIS and P(OPh)(3) were effectively realized to give the corresponding 2-deoxyglycosides in high yields.

  DOI：

  10.1021/acs.joc.5b01542
• 作为产物：
  描述：

  1,2-丙二醇 、 三乙基氯硅烷 在 (2R,4S)-3-((R)-cyclopentyl(1-methyl-1H-imidazol-2-yl)methyl)-4-isopropyl-2-methoxyoxazolidine 、 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88%的产率得到
  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.