6,1'-di-O-acetyl-4,3'-di-O-benzoyl-3-O-methoxymethyl-2-O-(3,4,6-tri-O-methoxymethyl-β-D-glucopyranosyl) sucrose | 942622-24-4

• 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: 6,1'-di-O-acetyl-4,3'-di-O-benzoyl-3-O-methoxymethyl-2-O-(3,4,6-tri-O-methoxymethyl-β-D-glucopyranosyl) sucrose
• 英文别名: [(2R,3R,4S,5R,6R)-2-(acetyloxymethyl)-6-[(2S,3S,4R,5R)-2-(acetyloxymethyl)-3-benzoyloxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5-[(2S,3R,4R,5R,6R)-3-hydroxy-4,5-bis(methoxymethoxy)-6-(methoxymethoxymethyl)oxan-2-yl]oxy-4-(methoxymethoxy)oxan-3-yl] benzoate
• CAS: 942622-24-4
• 化学式: C₄₄H₆₀O₂₄
• 分子量: 972.946
• InChiKey: WCISCOQAUOTAHO-LMEVWGSHSA-N

物化性质

• 沸点：
  942.3±65.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  68
• 可旋转键数：
  30
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  286
• 氢给体数：
  3
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  6,1'-di-O-acetyl-4,3'-di-O-benzoyl-3-O-methoxymethyl-2-O-(3,4,6-tri-O-methoxymethyl-β-D-glucopyranosyl) sucrose 在 溶剂黄146 作用下， 反应 8.0h， 以61%的产率得到6,1'-di-O-acetyl-4,3'-di-O-benzoyl-2-O-(β-D-glucopyranosyl) sucrose
  参考文献：
  名称：

  The first total synthesis of telephiose A

  摘要：

  The first total synthesis of telephiose A (1), a novel trisaccharide ester having two acetyl groups and two benzoyl groups, was achieved by using glucosyl donor 6 and disaccharide acceptor 12. The crucial key step was the stereoselective construction of the beta-D-glucosidic linkage featuring the neighboring group participation of the 2-O-N-phenylcarbamoyl group (of donor 6), which can be selectively deprotected in the presence of acetyl and benzoyl groups. Donor 6 was prepared from D-glucose in eight steps (33% yield), whereas acceptor 12 was prepared from sucrose in six steps (35% yield). Precursors 6 and 12 were reacted in subsequent reactions (five steps) to afford 1 in 22% yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.138
• 作为产物：
  描述：

  苯基-4,6-O-苯亚甲基-1-硫代-Β-D-吡喃葡萄糖苷 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 MS 4 Angstroem 、 四丁基氟化铵 、 溶剂黄146 、 N,N-二异丙基乙胺 、 四丁基亚硝酸铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 6,1'-di-O-acetyl-4,3'-di-O-benzoyl-3-O-methoxymethyl-2-O-(3,4,6-tri-O-methoxymethyl-β-D-glucopyranosyl) sucrose
  参考文献：
  名称：

  The first total synthesis of telephiose A

  摘要：

  The first total synthesis of telephiose A (1), a novel trisaccharide ester having two acetyl groups and two benzoyl groups, was achieved by using glucosyl donor 6 and disaccharide acceptor 12. The crucial key step was the stereoselective construction of the beta-D-glucosidic linkage featuring the neighboring group participation of the 2-O-N-phenylcarbamoyl group (of donor 6), which can be selectively deprotected in the presence of acetyl and benzoyl groups. Donor 6 was prepared from D-glucose in eight steps (33% yield), whereas acceptor 12 was prepared from sucrose in six steps (35% yield). Precursors 6 and 12 were reacted in subsequent reactions (five steps) to afford 1 in 22% yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.138