4,6-O-(di-tert-butylsilylene)-3-O-(N-hydroxy)carbamoyl-D-glucal | 1276537-62-2

• 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: 4,6-O-(di-tert-butylsilylene)-3-O-(N-hydroxy)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] N-hydroxycarbamate
• CAS: 1276537-62-2
• 化学式: C₁₅H₂₇NO₆Si
• 分子量: 345.468
• InChiKey: CRZNNJYVCHOGIB-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,6-O-(di-tert-butylsilylene)-3-O-(N-hydroxy)carbamoyl-D-glucal 在 吡啶 、 dirhodium tetraacetate 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 1,2-dideoxy-4,6-di-tert-butylsilylene-D-erythro-hex-1-enopyran-3-ulose
  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 62.0h， 生成 4,6-O-(di-tert-butylsilylene)-3-O-(N-hydroxy)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

• Osmium-Catalyzed Tethered Aminohydroxylation of Glycals: A Stereodirected Access to 2- and 3-Aminosugars
  作者：Stefania Mirabella、Francesca Cardona、Andrea Goti

  DOI：10.1021/ol503754f

  日期：2015.2.6

  The osmium-catalyzed aminohydroxylation of glycals has been achieved with complete regio- and stereocontrol by taking advantage of the Donohoe tethering approach. Glucals and galactals showed complementary reactivity in dependence of the stage at which the reaction was performed, i.e., directly or after double-bond shift consequent to a Ferrier rearrangement (that is, on the 1,2 or 2,3-unsaturated sugar), allowing access to both classes of 2-amino (mannosamine) and 3-amino (talosamine) sugar derivatives, respectively.
• 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.