3,4,6-tri-O-benzyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-D-glucopyranosyl N-(phenyl)trifluoroacetimidate | 1203584-67-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-benzyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-D-glucopyranosyl N-(phenyl)trifluoroacetimidate
• 英文别名: [(3R,4R,5S,6R)-3-[(4-nitrophenyl)sulfonylamino]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] 2,2,2-trifluoro-N-phenylethanimidate
• CAS: 1203584-67-1
• 化学式: C₄₁H₃₈F₃N₃O₉S
• 分子量: 805.829
• InChiKey: YIXSCEWWNCTYCQ-BJAYCDGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  159
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  tert-butyldiphenylsilyl 3,4,6-tri-O-benzyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-β-D-glucopyranose 在 四丁基氟化铵 、 caesium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.5h， 生成 3,4,6-tri-O-benzyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-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

文献信息

• Synthesis of Differentially Protected Glucosamine Building Blocks and Their Evaluation as Glycosylating Agents
  作者：Pascal Bindschadler、Lukas Dialer、Peter Seeberger

  DOI：10.1080/07328300903105108

  日期：2009.9

  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.