(2R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde | 191792-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde
• 英文别名: (2R,3R,4R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]oxolane-2-carbaldehyde
• CAS: 191792-26-4
• 化学式: C₁₇H₃₆O₄Si₂
• 分子量: 360.641
• InChiKey: QNFQEGYAUNNPAI-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde 在 吡啶 、 dimethyl sulfide borane 、 四丁基氟化铵 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 70.5h， 生成 Toluene-4-sulfonic acid (3R,4R,5S)-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Difuntionalised oxirane systems. Stereodivergent synthesis of 1,4;2,3-dianhydro-5-O-benzyl-l-lyxitol and -l-ribitol

  摘要：

  A simple, efficient, stereoselective synthesis of the diastereoisomeric cis/trans pair of difunctionalized 1,2-epoxides, 1,4;2,3-dianhydro-5-O-benzyl-L-lixitol 1 and 1,4;2,3-dianhydro-5-O-benzyl-L-ribitol 2 is described. Starting from D-(+)-xylose, the synthetic approach to 1 and 2 proceeds through the common intermediate, diol 6, and an appropriate sequence of selective functionalizations. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00136-5
• 作为产物：
  描述：

  (2R,3R,4R)-2-(Bis-isobutylsulfanyl-methyl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan 在 mercury dichloride 、 mercury(II) oxide 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以90%的产率得到(2R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde
  参考文献：
  名称：

  Difuntionalised oxirane systems. Stereodivergent synthesis of 1,4;2,3-dianhydro-5-O-benzyl-l-lyxitol and -l-ribitol

  摘要：

  A simple, efficient, stereoselective synthesis of the diastereoisomeric cis/trans pair of difunctionalized 1,2-epoxides, 1,4;2,3-dianhydro-5-O-benzyl-L-lixitol 1 and 1,4;2,3-dianhydro-5-O-benzyl-L-ribitol 2 is described. Starting from D-(+)-xylose, the synthetic approach to 1 and 2 proceeds through the common intermediate, diol 6, and an appropriate sequence of selective functionalizations. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00136-5

文献信息

• Difuntionalised oxirane systems. Stereodivergent synthesis of 1,4;2,3-dianhydro-5-O-benzyl-l-lyxitol and -l-ribitol
  作者：Paolo Crotti、Valeria Di Bussolo、Lucilla Favero、Claudia Gozzi、Mauro Pineschi

  DOI：10.1016/s0957-4166(97)00136-5

  日期：1997.5

  A simple, efficient, stereoselective synthesis of the diastereoisomeric cis/trans pair of difunctionalized 1,2-epoxides, 1,4;2,3-dianhydro-5-O-benzyl-L-lixitol 1 and 1,4;2,3-dianhydro-5-O-benzyl-L-ribitol 2 is described. Starting from D-(+)-xylose, the synthetic approach to 1 and 2 proceeds through the common intermediate, diol 6, and an appropriate sequence of selective functionalizations. (C) 1997 Elsevier Science Ltd.