3'-O-benzoyl-2,1':4,6-di-O-isopropylidene-3-O-methoxymethyl-4',6'-O-tetraisopropyldisiloxanilidene sucrose | 942622-18-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3'-O-benzoyl-2,1':4,6-di-O-isopropylidene-3-O-methoxymethyl-4',6'-O-tetraisopropyldisiloxanilidene sucrose
• 英文别名: [(1R,3R,6'aR,8R,9S,9'S,9'aR,10R,15S)-9-(methoxymethoxy)-6,6,12,12-tetramethyl-2',2',4',4'-tetra(propan-2-yl)spiro[2,5,7,11,13,16-hexaoxatricyclo[8.6.0.03,8]hexadecane-15,8'-6,6a,9,9a-tetrahydrofuro[3,2-f][1,3,5,2,4]trioxadisilocine]-9'-yl] benzoate
• CAS: 942622-18-6
• 化学式: C₃₉H₆₄O₁₄Si₂
• 分子量: 813.1
• InChiKey: QXZCODSSNGPWEZ-KKGIMQJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  55
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3'-O-benzoyl-2,1':4,6-di-O-isopropylidene-3-O-methoxymethyl-4',6'-O-tetraisopropyldisiloxanilidene sucrose 在 吡啶 、 盐酸 、 甲醇 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 MS 4 Angstroem 、 四丁基亚硝酸铵 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 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)-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 15.0h， 生成 3'-O-benzoyl-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