benzyl 2-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-β-D-glucopyranoside | 221190-07-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: benzyl 2-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3-hydroxy-2-(hydroxymethyl)-5,6-bis(phenylmethoxy)oxan-4-yl] 3,4,5-tris(phenylmethoxy)benzoate
• CAS: 221190-07-4
• 化学式: C₄₈H₄₆O₁₀
• 分子量: 782.887
• InChiKey: JVQJLUBEGIAKHV-UOLSNFROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  58
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (+/-)-hexabenzyloxydiphenic acid 、 benzyl 2-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以34%的产率得到benzyl 2-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-4,6-O-<(S)-2,2',3,3',4,4'-hexabenzyloxydiphenoyl>-β-D-glucopyranoside
  参考文献：
  名称：

  The First Total Syntheses of Enantiomerically Pure Naturally Occuring Ellagitannins Gemin D and its Regioisomer Hippomanin A

  摘要：

  The total syntheses of naturally occuring ellagitannins gemin D (1) and its regioisomer hippomanin A (2) are reported. In addition, the phase-transfer catalyzed benzylation reaction of the 2,3-glucopyranoside diols 3-7 is described. Our studies have illustrated the influence of the structure of 2,3-glucopyranoside diols on the regioselectivity of the phase-transfer catalyzed benzylation at their free 2,3-OH groups. We could show, that both phase-transfer catalyzed benzylations of 2,3-glucopyranoside diols using tetrabutylammonium hydrogensulfate (Bu4NHSO4) or using tetrabutylammonium iodide (Bu4NI) disfavour the formation of the corresponding 3-O-monobenzylated products and preferentially give the 2-O-monobenzylated products. However, the ratio of the generated 2- versus 3-O-mono- and 2,3-dibenzylated products from these reactions also strongly depends upon the nature of the starting materials. The glucopyranosides 3 and 4 are the first examples, which allow the completely regioselective monobenzyIation at the 2-OH positions by a phase-transfer catalyzed reaction.

  DOI：

  10.1002/(sici)1521-3897(199902)341:2<159::aid-prac159>3.0.co;2-6
• 作为产物：
  描述：

  3,4,5-三苄氧基苯甲酸 在 四丁基碘化铵 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 55.0h， 生成 benzyl 2-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-β-D-glucopyranoside
  参考文献：
  名称：

  The First Total Syntheses of Enantiomerically Pure Naturally Occuring Ellagitannins Gemin D and its Regioisomer Hippomanin A

  摘要：

  The total syntheses of naturally occuring ellagitannins gemin D (1) and its regioisomer hippomanin A (2) are reported. In addition, the phase-transfer catalyzed benzylation reaction of the 2,3-glucopyranoside diols 3-7 is described. Our studies have illustrated the influence of the structure of 2,3-glucopyranoside diols on the regioselectivity of the phase-transfer catalyzed benzylation at their free 2,3-OH groups. We could show, that both phase-transfer catalyzed benzylations of 2,3-glucopyranoside diols using tetrabutylammonium hydrogensulfate (Bu4NHSO4) or using tetrabutylammonium iodide (Bu4NI) disfavour the formation of the corresponding 3-O-monobenzylated products and preferentially give the 2-O-monobenzylated products. However, the ratio of the generated 2- versus 3-O-mono- and 2,3-dibenzylated products from these reactions also strongly depends upon the nature of the starting materials. The glucopyranosides 3 and 4 are the first examples, which allow the completely regioselective monobenzyIation at the 2-OH positions by a phase-transfer catalyzed reaction.

  DOI：

  10.1002/(sici)1521-3897(199902)341:2<159::aid-prac159>3.0.co;2-6