4,6-O-(di-tert-butylsilylene)-3-O-(N-tosyloxy)carbamoyl-D-glucal | 1276537-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,6-O-(di-tert-butylsilylene)-3-O-(N-tosyloxy)carbamoyl-D-glucal
• 英文别名: [[(4aR,8R,8aS)-2,2-ditert-butyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasilin-8-yl]oxycarbonylamino] 4-methylbenzenesulfonate
• CAS: 1276537-63-3
• 化学式: C₂₂H₃₃NO₈SSi
• 分子量: 499.657
• InChiKey: MKMBHXKBJXYNJI-QRVBRYPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,6-O-(di-tert-butylsilylene)-3-O-(N-tosyloxy)carbamoyl-D-glucal 在 dirhodium tetraacetate 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 以10%的产率得到3-O-carbamoyl-4,6-O-di-tert-butylsilylene-D-glucal
  参考文献：
  名称：

  Dihydropyranone Formation by Ipso C−H Activation in a Glucal 3-Carbamate-Derived Rhodium Acyl Nitrenoid

  摘要：

  By using (N-tosyloxy)-3-O-carbamoyl-o-glucal 10, which removes the :need for a hypervalentsiodine (III) oxidant, we provide evidence for rhodium nitrenoid-mediated ipso C-H activation as the origin of a C3oxidized dihydropyranone product 3. This system may be especially susceptible to such a pathway because of the ease of forming a cation upon hydride transfer to the rhodium-complexed acyl nitrene.

  DOI：

  10.1021/jo101599q
• 作为产物：
  描述：

  4,6-O-di(tert-butyl)silanediyl-D-glucal 在 吡啶 、 盐酸羟胺 作用下， 以 二氯甲烷 为溶剂， 反应 66.5h， 生成 4,6-O-(di-tert-butylsilylene)-3-O-(N-tosyloxy)carbamoyl-D-glucal
  参考文献：
  名称：

  Dihydropyranone Formation by Ipso C−H Activation in a Glucal 3-Carbamate-Derived Rhodium Acyl Nitrenoid

  摘要：

  By using (N-tosyloxy)-3-O-carbamoyl-o-glucal 10, which removes the :need for a hypervalentsiodine (III) oxidant, we provide evidence for rhodium nitrenoid-mediated ipso C-H activation as the origin of a C3oxidized dihydropyranone product 3. This system may be especially susceptible to such a pathway because of the ease of forming a cation upon hydride transfer to the rhodium-complexed acyl nitrene.

  DOI：

  10.1021/jo101599q

文献信息

• Dihydropyranone Formation by <i>Ipso</i> C−H Activation in a Glucal 3-Carbamate-Derived Rhodium Acyl Nitrenoid
  作者：Brisa Hurlocker、Nadia C. Abascal、Lindsay M. Repka、Elsy Santizo-Deleon、Abigail L. Smenton、Victoria Baranov、Ritu Gupta、Sarah E. Bernard、Shenjuti Chowdhury、Christian M. Rojas

  DOI：10.1021/jo101599q

  日期：2011.4.1

  By using (N-tosyloxy)-3-O-carbamoyl-o-glucal 10, which removes the :need for a hypervalentsiodine (III) oxidant, we provide evidence for rhodium nitrenoid-mediated ipso C-H activation as the origin of a C3oxidized dihydropyranone product 3. This system may be especially susceptible to such a pathway because of the ease of forming a cation upon hydride transfer to the rhodium-complexed acyl nitrene.