(R)-1-(trityloxy)but-3-en-2-ol | 578716-73-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (R)-1-(trityloxy)but-3-en-2-ol
• 英文别名: (R)-1-(triphenylmethoxy)-3-buten-2-ol；(2R)-1-trityloxybut-3-en-2-ol
• CAS: 578716-73-1
• 化学式: C₂₃H₂₂O₂
• 分子量: 330.426
• InChiKey: BXJGLPROAVAGKO-JOCHJYFZSA-N

物化性质

• 沸点：
  465.9±33.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  (R)-1-(trityloxy)but-3-en-2-ol 在 Grubbs catalyst first generation sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (R)-2-Trityloxymethyl-2,5-dihydro-furan
  参考文献：
  名称：

  Stereoselective synthesis of l-isonucleosides

  摘要：

  L-Isonucleosides 17 and 19 were stereoselectively synthesised from (S)-glycidol by two different procedures. The key step was the synthesis of a chiral dihydrofuran which was carried out by oxidation/elimination of 8 and by ring-closing metathesis of diene 10. The procedure can be applied to the synthesis of both enantiomers. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00743-3
• 作为产物：
  描述：

  (E)-methyl (4-(trityloxy)but-2-en-1-yl)carbonate 在 CF₃O₃S^(1-)*C₅₈H₅₂IrNO₄P⁽¹⁺⁾ 、 potassium hydrogencarbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以87%的产率得到(R)-1-(trityloxy)but-3-en-2-ol
  参考文献：
  名称：

  Enantio- and Regioselective Iridium-Catalyzed Allylic Hydroxylation

  摘要：

  The first enantioselective allylic hydroxylation to prepare branched allylic alcohols directly is described. Bicarbonate was used as nucleophile in conjunction with new single component Ir-catalysts, which are stable to air and water. Excellent regio- and enantioselectivities have been achieved with a representative set of substrates.

  DOI：

  10.1021/ja109953v

文献信息

• <i>P</i>-Stereogenic Bicyclo[4.3.1]phosphite Boranes: Synthesis and Utility of Tunable <i>P</i>-Tether Systems for the Desymmetrization of <i>C</i>₂-Symmetric 1,3-<i>anti</i>-Diols
  作者：Jana L. Markley、Paul R. Hanson

  DOI：10.1021/acs.orglett.7b00851

  日期：2017.5.19

  1]phosphite borane tether systems for the desymmetrization of C2-symmetric dienediols is reported. This report highlights preliminary studies including tether installation and removal as well as chemoselective functionalization of the exocyclic olefin via diimide reduction or cross-metathesis. Most notably, a divergent oxidation strategy allows for the transformation of the bicyclic phosphite borane complexes

  报道了用于C 2对称二烯二醇去对称化的P-立体异构双环[4.3.1]亚磷酸硼烷系链系统的开发。该报告重点介绍了初步研究，包括系链的安装和去除以及通过二酰亚胺还原或交叉复分解实现的环外烯烃的化学选择性官能化。最值得注意的是，发散的氧化策略允许将双环亚磷酸酯硼烷络合物转化为相应的磷酸盐或硫代磷酸盐系统，从而突出了该P-系链系统的电子衰减。
• Synthesis and Stereospecificity of 4,5-Disubstituted Oxazolidinone Ligands Binding to T-box Riboswitch RNA
  作者：Crina M. Orac、Shu Zhou、John A. Means、David Boehm、Stephen C. Bergmeier、Jennifer V. Hines

  DOI：10.1021/jm2006904

  日期：2011.10.13

  The enantiomers and the cis isomers of two previously studied 4,5-disubstituted oxazolidinones have been synthesized, and their binding to the T-box riboswitch antiterminator model RNA has been investigated in detail. Characterization of ligand affinities and binding site localization indicates that there is little stereospecific discrimination for binding antiterminator RNA alone. This binding similarity between enantiomers is likely due to surface binding, which accommodates ligand conformations 1 that result in comparable ligand-antiterminator contacts. These results have significant implications for T-box antiterminator-targeted drug discovery and, in general, for targeting other medicinally relevant RNA that do not present deep binding pockets.
• Enantio- and Regioselective Iridium-Catalyzed Allylic Hydroxylation
  作者：Martin Gärtner、Steffen Mader、Kai Seehafer、Günter Helmchen

  DOI：10.1021/ja109953v

  日期：2011.2.23

  The first enantioselective allylic hydroxylation to prepare branched allylic alcohols directly is described. Bicarbonate was used as nucleophile in conjunction with new single component Ir-catalysts, which are stable to air and water. Excellent regio- and enantioselectivities have been achieved with a representative set of substrates.
• Stereoselective synthesis of l-isonucleosides
  作者：Sı́lvia Aragonès、Fernando Bravo、Yolanda Dı́az、Ma̱ Isabel Matheu、Sergio Castillón

  DOI：10.1016/s0040-4039(03)00743-3

  日期：2003.5

  L-Isonucleosides 17 and 19 were stereoselectively synthesised from (S)-glycidol by two different procedures. The key step was the synthesis of a chiral dihydrofuran which was carried out by oxidation/elimination of 8 and by ring-closing metathesis of diene 10. The procedure can be applied to the synthesis of both enantiomers. (C) 2003 Elsevier Science Ltd. All rights reserved.