2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→6)]-2,4-di-O-acetyl-D-glucopyranosyl trichloroacetimidate | 1462884-73-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→6)]-2,4-di-O-acetyl-D-glucopyranosyl trichloroacetimidate
• CAS: 1462884-73-6
• 化学式: C₅₈H₅₈Cl₃NO₂₄
• 分子量: 1259.45
• InChiKey: PYUHZVJWQMSAMB-WBMFYUPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  86.0
• 可旋转键数：
  20.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  315.93
• 氢给体数：
  1.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→6)]-2,4-di-O-acetyl-D-glucopyranosyl trichloroacetimidate 、 2-(3-甲氧基-4-苯基甲氧基苯基)乙醇 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以68%的产率得到3-methoxyl-4-benzoxylphenylethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→6)]-2,4-di-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Leonosides E and F derived from Leonurus japonicas Houtt

  摘要：

  Leonosides E and F, two natural phenylethanoid glycosides derived from Leonurus japonicas Houtt, which bear different trisaccharide moieties-one linear and one branched, were totally synthesized via a direct transglycosylation strategy. After trisaccharyl trichloroacetimidates 3 and 4 were prepared as glycosyl donors, they were coupled with the homovanillyl aglycon via silver triflate-promoted transglycosylation to successfully furnish the fully protected glycosides, which were globally deprotected to afford the target molecules in 6.77% and 10.08% overall yields for the longest linear synthetic sequence starting from 6 and 14. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.07.012
• 作为产物：
  描述：

  在 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→6)]-2,4-di-O-acetyl-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of Leonosides E and F derived from Leonurus japonicas Houtt

  摘要：

  Leonosides E and F, two natural phenylethanoid glycosides derived from Leonurus japonicas Houtt, which bear different trisaccharide moieties-one linear and one branched, were totally synthesized via a direct transglycosylation strategy. After trisaccharyl trichloroacetimidates 3 and 4 were prepared as glycosyl donors, they were coupled with the homovanillyl aglycon via silver triflate-promoted transglycosylation to successfully furnish the fully protected glycosides, which were globally deprotected to afford the target molecules in 6.77% and 10.08% overall yields for the longest linear synthetic sequence starting from 6 and 14. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.07.012