2,1':4,6-di-O-isopropylidene-3-O-methoxymethyl-4',6'-O-tetraisopropyldisiloxanilidene sucrose | 942622-17-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,1':4,6-di-O-isopropylidene-3-O-methoxymethyl-4',6'-O-tetraisopropyldisiloxanilidene sucrose
• CAS: 942622-17-5
• 化学式: C₃₂H₆₀O₁₃Si₂
• 分子量: 708.992
• InChiKey: XKJJQQMNCTXKFJ-YZPGTCFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  47.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  130.99
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2,1':4,6-di-O-isopropylidene-3-O-methoxymethyl-4',6'-O-tetraisopropyldisiloxanilidene sucrose 在 吡啶 、 盐酸 、 甲醇 作用下， 反应 3.0h， 生成 3'-O-benzoyl-3-O-methoxymethyl-4',6'-O-tetraisopropyldisiloxanilidene 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：

  2,1':4,6-di-O-isopropylidene sucrose 在 吡啶 、 咪唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 2,1':4,6-di-O-isopropylidene-3-O-methoxymethyl-4',6'-O-tetraisopropyldisiloxanilidene 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