| 1561047-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1561047-70-8
• 化学式: C₁₉H₃₀O₃Si
• 分子量: 334.531
• InChiKey: IKNLWHGBJJTBBF-RYQLBKOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  在 三苯基膦氢溴酸盐 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.27h， 以77%的产率得到3-O-(tert-butyldimethylsilyl)oxy-4-O-benzyl-L-oliose
  参考文献：
  名称：

  Automated, Multistep Continuous‐Flow Synthesis of 2,6‐Dideoxy and 3‐Amino‐2,3,6‐trideoxy Monosaccharide Building Blocks

  摘要：

  AbstractAn automated continuous flow system capable of producing protected deoxy‐sugar donors from commercial material is described. Four 2,6‐dideoxy and two 3‐amino‐2,3,6‐trideoxy sugars with orthogonal protecting groups were synthesized in 11–32 % overall yields in 74–131.5 minutes of total reaction time. Several of the reactions were able to be concatenated into a continuous process, avoiding the need for chromatographic purification of intermediates. The modular nature of the experimental setup allowed for reaction streams to be split into different lines for the parallel synthesis of multiple donors. Further, the continuous flow processes were fully automated and described through the design of an open‐source Python‐controlled automation platform.

  DOI：

  10.1002/anie.202109887
• 作为产物：
  描述：

  6-deoxy-L-galactose 在 甲醇 、 4-二甲氨基吡啶 、 乙酰溴 、 sodium methylate 、 sodium hexamethyldisilazane 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.98h， 生成
  参考文献：
  名称：

  Automated, Multistep Continuous‐Flow Synthesis of 2,6‐Dideoxy and 3‐Amino‐2,3,6‐trideoxy Monosaccharide Building Blocks

  摘要：

  AbstractAn automated continuous flow system capable of producing protected deoxy‐sugar donors from commercial material is described. Four 2,6‐dideoxy and two 3‐amino‐2,3,6‐trideoxy sugars with orthogonal protecting groups were synthesized in 11–32 % overall yields in 74–131.5 minutes of total reaction time. Several of the reactions were able to be concatenated into a continuous process, avoiding the need for chromatographic purification of intermediates. The modular nature of the experimental setup allowed for reaction streams to be split into different lines for the parallel synthesis of multiple donors. Further, the continuous flow processes were fully automated and described through the design of an open‐source Python‐controlled automation platform.

  DOI：

  10.1002/anie.202109887

文献信息

• Direct Synthesis of 2-Deoxy-β-Glycosides via Anomeric <i>O</i>-Alkylation with Secondary Electrophiles
  作者：Danyang Zhu、Kedar N. Baryal、Surya Adhikari、Jianglong Zhu

  DOI：10.1021/ja4116956

  日期：2014.2.26

  An approach for direct synthesis of biologically significant 2-deoxy-beta-glycosides has been developed via O-alkylation of a variety of 2-deoxy-sugar-derived anomeric alkoxides using challenging secondary triflates as electrophiles. It was found a free hydroxyl group at C3 of the 2-deoxy-sugar-derived lactols is required in order to achieve synthetically efficient yields. This method has also been applied to the convergent synthesis of a 2-deoxy-beta-tetrasaccharide.