3,4,6-tri-O-acetyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-β-D-glucopyranosyl N-(phenyl)trifluoroacetimidate | 1203584-66-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-β-D-glucopyranosyl N-(phenyl)trifluoroacetimidate
• CAS: 1203584-66-0
• 化学式: C₂₆H₂₆F₃N₃O₁₂S
• 分子量: 661.567
• InChiKey: MHOCAYYPJATRRJ-RMRNXIRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  45.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  199.03
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 3,4,6-tri-O-acetyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-β-D-glucopyranosyl N-(phenyl)trifluoroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以63%的产率得到methyl 3,4,6-tri-O-acetyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Differentially Protected Glucosamine Building Blocks and Their Evaluation as Glycosylating Agents

  摘要：

  The modular assembly of heparin oligosaccharides requires glucosamine building blocks with amine protecting groups for a-selective glycosylations that can be readily removed. The synthesis of N-4-nitrobenzensulphonamide (nosyl)- and N-2,4-dinitrophenyl (DNP)-protected glucosamine building blocks and their evaluation as glycosylating agents is described. The N-nosyl-protected glucosamine building blocks were challenging to prepare and their glycosylations resulted in inseparable mixtures of products. The N-DNP-protected glucosamines, however, were readily synthesized and resulted in a-selective couplings to protected L-iduronic acid derivatives.

  DOI：

  10.1080/07328300903105108
• 作为产物：
  描述：

  1-O-tert-butyldiphenylsilyl-3,4,6-tri-O-acetyl-2-deoxy-2-amino-β-D-glucopyranoside 在 四丁基氟化铵 、 caesium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 3,4,6-tri-O-acetyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-β-D-glucopyranosyl N-(phenyl)trifluoroacetimidate
  参考文献：
  名称：

  Synthesis of Differentially Protected Glucosamine Building Blocks and Their Evaluation as Glycosylating Agents

  摘要：

  The modular assembly of heparin oligosaccharides requires glucosamine building blocks with amine protecting groups for a-selective glycosylations that can be readily removed. The synthesis of N-4-nitrobenzensulphonamide (nosyl)- and N-2,4-dinitrophenyl (DNP)-protected glucosamine building blocks and their evaluation as glycosylating agents is described. The N-nosyl-protected glucosamine building blocks were challenging to prepare and their glycosylations resulted in inseparable mixtures of products. The N-DNP-protected glucosamines, however, were readily synthesized and resulted in a-selective couplings to protected L-iduronic acid derivatives.

  DOI：

  10.1080/07328300903105108