phenyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside

• 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-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-6-phenoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• 化学式: C₃₃H₃₄O₆
• 分子量: 526.629
• InChiKey: HSNXRAGPIRAXPR-IZDBAANZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside 在 sodium azide 、 对甲苯磺酸 、 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 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

文献信息

• NON-ANOMERIC SUGAR ISOUREAS
  作者：Christian Sowa、Ralf Miethchen、Helmut Reinke

  DOI：10.1081/car-120013497

  日期：2002.9.23

  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.