(2R)-2-(tert-butyldiphenyl)silyloxymethyl-2,5-dihydrofuran | 494834-49-0

• 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)-2-(tert-butyldiphenyl)silyloxymethyl-2,5-dihydrofuran
• 英文别名: tert-butyl-[[(2R)-2,5-dihydrofuran-2-yl]methoxy]-diphenylsilane
• CAS: 494834-49-0
• 化学式: C₂₁H₂₆O₂Si
• 分子量: 338.522
• InChiKey: WWVFACXVTDIKMA-GOSISDBHSA-N

物化性质

• 熔点：
  40-42 °C
• 沸点：
  397.5±42.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-2-(tert-butyldiphenyl)silyloxymethyl-2,5-dihydrofuran 在 ruthenium trichloride 、 sodium periodate 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 3.0h， 以35%的产率得到(S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3,4-diol
  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：

  4-phenylselenenyl-2-(tert-butyldiphenyl)silyloxymethyl-tetrahydrofuran 在 吡啶 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以92%的产率得到(2R)-2-(tert-butyldiphenyl)silyloxymethyl-2,5-dihydrofuran
  参考文献：
  名称：

  An Expeditious and Efficient Procedure for the Synthesis of Unsaturated Acyclonucleosides of Z Configuration Related to D4T

  摘要：

  Enantiopure 2,5-dihydrofuran derivatives were prepared from (S)-glycidol through a new reaction sequence involving epoxide opening with a vinyleuprate, selenium-induced cyclization to give exclusively the 5-endo product, and regioselective selenoxide elimination. Unsaturated acy-clonucleosides of Z configuration were obtained in a straightforward manner by treating 2,5-dihydrofuran with iodotrimethylsilane in the presence of silylated purinic or pyrimidinic bases. This synthetic process involves opening of the dihydrofuran ring by trimethylsilyl iodide and substitution of iodine by the nucleic base in a single reaction step.

  DOI：

  10.1021/jo010948r

文献信息

• 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.
• An Expeditious and Efficient Procedure for the Synthesis of Unsaturated Acyclonucleosides of <i>Z</i> Configuration Related to D4T
  作者：Fernando Bravo、Antonio Viso、Sergio Castillón

  DOI：10.1021/jo010948r

  日期：2003.2.1

  Enantiopure 2,5-dihydrofuran derivatives were prepared from (S)-glycidol through a new reaction sequence involving epoxide opening with a vinyleuprate, selenium-induced cyclization to give exclusively the 5-endo product, and regioselective selenoxide elimination. Unsaturated acy-clonucleosides of Z configuration were obtained in a straightforward manner by treating 2,5-dihydrofuran with iodotrimethylsilane in the presence of silylated purinic or pyrimidinic bases. This synthetic process involves opening of the dihydrofuran ring by trimethylsilyl iodide and substitution of iodine by the nucleic base in a single reaction step.