isopropyl 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1→2)-3,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside | 1462884-65-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: isopropyl 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1→2)-3,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside
• 英文别名: [(2S,3S,4R,5R,6S)-4-benzoyloxy-2-methyl-6-propan-2-ylsulfanyl-5-[(2S,3R,4S,5S)-3,4,5-triacetyloxyoxan-2-yl]oxyoxan-3-yl] benzoate
• CAS: 1462884-65-6
• 化学式: C₃₄H₄₀O₁₃S
• 分子量: 688.75
• InChiKey: NKYGINRLVAQEKS-XFQOOSLXSA-N

物化性质

• 沸点：
  720.3±60.0 °C(predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  185
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  isopropyl 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1→2)-3,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 生成 C₃₇H₄₄O₁₉
  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：

  isopropyl 4-O-benzoyl-1-thio-α-L-rhamnopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.84h， 生成 isopropyl 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1→2)-3,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside
  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

文献信息

• Synthesis of Leonosides E and F derived from Leonurus japonicas Houtt
  作者：Guofeng Gu、Yisheng Zhao、Zhongwu Guo

  DOI：10.1016/j.carres.2013.07.012

  日期：2013.10

  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.