(2R)-1-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxybut-3-en-2-ol | 136984-32-2

• 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: (2R)-1-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxybut-3-en-2-ol
• CAS: 136984-32-2
• 化学式: C₁₂H₂₆O₂Si
• 分子量: 230.423
• InChiKey: GDKZWTACARSUPU-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  苯甲酰氯 、 (2R)-1-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxybut-3-en-2-ol 在 吡啶 作用下， 反应 17.0h， 以95%的产率得到Benzoic acid (R)-1-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-allyl ester
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiomerically pure alkene 1,2-diols and glycosides thereof

  摘要：

  The kinetic resolution of racemic 2-O-acylated 3-butene-1,2-diol and 1-O-acylated 3-butene-1,2-diol derivatives by enzymatic saponification and enzymatic esterification, respectively, is investigated with several lipases and esterases. The resulting partially blocked enantiomers are glycosylated with glycosyl halides and trichloroacetimidates, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00051-2
• 作为产物：
  描述：

  二甲基叔己基氯化硅 在 吡啶 、 咪唑 、 sodium hydroxide 、 phosphate buffer 、 Pseudomonas Amano PS lipase 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 (2R)-1-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxybut-3-en-2-ol
  参考文献：
  名称：

  Chemoenzymatic synthesis of enantiomerically pure alkene 1,2-diols and glycosides thereof

  摘要：

  The kinetic resolution of racemic 2-O-acylated 3-butene-1,2-diol and 1-O-acylated 3-butene-1,2-diol derivatives by enzymatic saponification and enzymatic esterification, respectively, is investigated with several lipases and esterases. The resulting partially blocked enantiomers are glycosylated with glycosyl halides and trichloroacetimidates, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00051-2

文献信息

• Enzymatic preparation of enantiomerically pure and selectively protected 1,2- and 1,3-diols
  作者：Ulrich Goergens、Manfred P. Schneider

  DOI：10.1039/c39910001066

  日期：——

  The optically pure, selectively protected 1,2- and 1,3-diol derivatives (R)- and (S)-1–8 have been prepared by enzymatic hydrolysis of their racemic acetates and chloroacetates in the presence of ester hydrolase from Pseudomonas fluorescens(SAM-1).

  在荧光假单胞菌（SAM-1）的酯水解酶作用下，通过酶水解外消旋乙酸酯和氯乙酸酯，制备出光学纯度高、选择性保护的 1,2- 和 1,3- 二醇衍生物 (R)- 和 (S)-1-8。
• Chemoenzymatic synthesis of enantiomerically pure alkene 1,2-diols and glycosides thereof
  作者：Thomas Ziegler、Frank Bien、Claus Jurisch

  DOI：10.1016/s0957-4166(98)00051-2

  日期：1998.3

  The kinetic resolution of racemic 2-O-acylated 3-butene-1,2-diol and 1-O-acylated 3-butene-1,2-diol derivatives by enzymatic saponification and enzymatic esterification, respectively, is investigated with several lipases and esterases. The resulting partially blocked enantiomers are glycosylated with glycosyl halides and trichloroacetimidates, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.