2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1→2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2,4,6-tri-O-acetyl-D-glucopyranosyl trichloroacetimidate | 1462884-68-9

• 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-arabinopyranosyl-(1→2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2,4,6-tri-O-acetyl-D-glucopyranosyl trichloroacetimidate
• 英文别名: Ara2Ac3Ac4Ac(a1-2)[Bz(-3)][Bz(-4)]Rha(a1-3)Glc2Ac4Ac6Ac(a)-O-C(NH)CCl3；[(2S,3S,4R,5R,6S)-4-benzoyloxy-6-[(2R,3R,4S,5R,6R)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl]oxy-2-methyl-5-[(2S,3R,4S,5S)-3,4,5-triacetyloxyoxan-2-yl]oxyoxan-3-yl] benzoate
• CAS: 1462884-68-9
• 化学式: C₄₅H₅₀Cl₃NO₂₂
• 分子量: 1063.24
• InChiKey: XSFXCHCRFJXMJI-ZOPWEYFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  71
• 可旋转键数：
  25
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  290
• 氢给体数：
  1
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1→2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2,4,6-tri-O-acetyl-D-glucopyranosyl trichloroacetimidate 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成
  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：

  Ara2Ac3Ac4Ac(a1-2)[Bz(-3)][Bz(-4)]Rha(a1-3)Glc1Ac2Ac4Ac6Ac 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 3.5h， 生成 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1→2)-3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2,4,6-tri-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