1,5-anhydro-3-O-benzoyl-6-O-[tert-butyl(dimethyl)silyl]-2-deoxy-D-arabino-hex-1-enitol | 114861-44-8

• 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: 1,5-anhydro-3-O-benzoyl-6-O-[tert-butyl(dimethyl)silyl]-2-deoxy-D-arabino-hex-1-enitol
• 英文别名: [(2R,3S,4R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-3,4-dihydro-2H-pyran-4-yl] benzoate
• CAS: 114861-44-8
• 化学式: C₁₉H₂₈O₅Si
• 分子量: 364.514
• InChiKey: FRSIMGJARWCVSR-ZACQAIPSSA-N

物化性质

• 沸点：
  438.2±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-3-O-benzoyl-6-O-[tert-butyl(dimethyl)silyl]-2-deoxy-D-arabino-hex-1-enitol 在 甲酸 、 氯磺酰异氰酸酯 作用下， 以 N,N-二甲基乙酰胺 、 乙腈 为溶剂， 以79%的产率得到(2R,3S,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3-(sulfamoyloxy)-3,4-dihydro-2H-pyran-4-yl benzoate
  参考文献：
  名称：

  通过铑催化和基质控制的糖基叠氮基团 高度立体选择性地合成氨基糖苷†

  摘要：

  传达了氨基磺酸酯在C3，C4或C6处接近α-或β-氨基糖苷类的糖基支架上的灵活安装方式。应用了多种糖基受体（O，S和N），从而增强了该方法作为立体选择性合成多官能化α-或β-氨基糖的操作简单方案的实用性。

  DOI：

  10.1039/b823099b
• 作为产物：
  描述：

  D-葡萄烯糖 在 吡啶 、 咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 生成 1,5-anhydro-3-O-benzoyl-6-O-[tert-butyl(dimethyl)silyl]-2-deoxy-D-arabino-hex-1-enitol
  参考文献：
  名称：

  Radical cyclization routes to bridged pyranosides as precursors of densely functionalized cycloalkanes

  摘要：

  Glycals derived from hexopyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group. Radical cyclization of these functionalities leads to bicyclic systems whose bridge sizes depend on the lengths of the olefinic appendages. Hydrolysis of the anomeric centers of the [2.2.1] structures leads spontaneously to cyclopentane derivatives. However, with [2.2.2] structures, the hemiacetal intermediates are stable in bicyclic forms but are opened readily upon mcerpatolysis with propane dithiol to give cyclohexane derivatives.

  DOI：

  10.1021/jo00028a033

文献信息

• Kjoelberg, Ove; Neumann, Klaus, Acta Chemica Scandinavica, 1993, vol. 47, # 8, p. 843 - 845
  作者：Kjoelberg, Ove、Neumann, Klaus

  DOI：——

  日期：——
• Highly stereoselective synthesis of aminoglycosides via rhodium-catalyzed and substrate-controlled aziridination of glycals
  作者：Rujee Lorpitthaya、K. B. Sophy、Jer-Lai Kuo、Xue-Wei Liu

  DOI：10.1039/b823099b

  日期：——

  C3, C4, or C6 approaching α- or β-aminoglycosides is communicated. A variety of glycal acceptors (O, S, and N) were applied, enhancing the utility of this method as an operationally simple protocol for the stereoselective synthesis of polyfunctionalized α- or β- aminosaccharides.

  传达了氨基磺酸酯在C3，C4或C6处接近α-或β-氨基糖苷类的糖基支架上的灵活安装方式。应用了多种糖基受体（O，S和N），从而增强了该方法作为立体选择性合成多官能化α-或β-氨基糖的操作简单方案的实用性。
• Radical cyclization routes to bridged pyranosides as precursors of densely functionalized cycloalkanes
  作者：R. A. Alonso、G. D. Vite、R. E. McDevitt、B. Fraser-Reid

  DOI：10.1021/jo00028a033

  日期：1992.1

  Glycals derived from hexopyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group. Radical cyclization of these functionalities leads to bicyclic systems whose bridge sizes depend on the lengths of the olefinic appendages. Hydrolysis of the anomeric centers of the [2.2.1] structures leads spontaneously to cyclopentane derivatives. However, with [2.2.2] structures, the hemiacetal intermediates are stable in bicyclic forms but are opened readily upon mcerpatolysis with propane dithiol to give cyclohexane derivatives.