phenyl 2,3,4-tri-O-benzyl-6-O-(N,N'-dicyclohexylisoureido)-β-D-glucopyranoside | 492448-82-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4-tri-O-benzyl-6-O-(N,N'-dicyclohexylisoureido)-β-D-glucopyranoside
• CAS: 492448-82-5
• 化学式: C₄₆H₅₆N₂O₆
• 分子量: 732.96
• InChiKey: WJRMSWQCNJSNIG-XVQIYQHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.17
• 重原子数：
  54.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  79.77
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-benzyl-6-O-(N,N'-dicyclohexylisoureido)-β-D-glucopyranoside 在 sodium azide 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以95%的产率得到phenyl 6-azido-6-deoxy-2,3,4-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  NON-ANOMERIC SUGAR ISOUREAS

  摘要：

  Six non-anomeric isourea derivatives Of D-fructose (7, 8), D-glucose (9, 10), 6-deoxy-L-altrose (11) and L-rhamnose (12) were synthesized from the precursors 1-6 by a CuCl-catalyzed addition of a non-glycosidic OH-group to DCC and DIPC, respectively. Subsequently, the isoureido group of phenyl 2,3,4-tri-O-benzyl-6-O-(N,N'-dicyclohexylisoureido)-beta-D-glucopyranoside (10) was replaced by an azido and a thioacetyl group, respectively, yielding the corresponding 6-deoxy-6-azido-D-glucopyranoside (13) and 6-deoxy-6-thioacetyl-D-glucopyranoside (14) in moderate to good yields.

  DOI：

  10.1081/car-120013497
• 作为产物：
  描述：

  N,N'-二环己基碳二亚胺 、 phenyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside 在 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以77%的产率得到phenyl 2,3,4-tri-O-benzyl-6-O-(N,N'-dicyclohexylisoureido)-β-D-glucopyranoside
  参考文献：
  名称：

  NON-ANOMERIC SUGAR ISOUREAS

  摘要：

  Six non-anomeric isourea derivatives Of D-fructose (7, 8), D-glucose (9, 10), 6-deoxy-L-altrose (11) and L-rhamnose (12) were synthesized from the precursors 1-6 by a CuCl-catalyzed addition of a non-glycosidic OH-group to DCC and DIPC, respectively. Subsequently, the isoureido group of phenyl 2,3,4-tri-O-benzyl-6-O-(N,N'-dicyclohexylisoureido)-beta-D-glucopyranoside (10) was replaced by an azido and a thioacetyl group, respectively, yielding the corresponding 6-deoxy-6-azido-D-glucopyranoside (13) and 6-deoxy-6-thioacetyl-D-glucopyranoside (14) in moderate to good yields.

  DOI：

  10.1081/car-120013497