(2R,3S,4S,5R,6R)-6-(acetoxymethyl)-3-(((3aS,4R,5aR,9aR,9bS)-2,2,8,8-tetramethylhexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yl)oxy)tetrahydro-2H-pyran-2,4,5-triyl triacetate | 1356346-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6R)-6-(acetoxymethyl)-3-(((3aS,4R,5aR,9aR,9bS)-2,2,8,8-tetramethylhexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yl)oxy)tetrahydro-2H-pyran-2,4,5-triyl triacetate
• CAS: 1356346-72-9
• 化学式: C₂₆H₃₈O₁₅
• 分子量: 590.579
• InChiKey: KMSXWTULZCHDIG-WCOSSBOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.48
• 重原子数：
  41.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  169.81
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  [(1R,2S,6S,7R,9R)-4,4,12,12-tetramethyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecan-7-yl] 2,2,2-trichloroethanimidate 、 1,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 indium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以94%的产率得到(2R,3S,4S,5R,6R)-6-(acetoxymethyl)-3-(((3aS,4R,5aR,9aR,9bS)-2,2,8,8-tetramethylhexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-yl)oxy)tetrahydro-2H-pyran-2,4,5-triyl triacetate
  参考文献：
  名称：

  Using In(III) as a promoter for glycosylation

  摘要：

  InCl3, InBr3, and In(OTf)(3) were tested as promoters in the preparation of glycosides from trichloroacetimidate precursors. A range of protecting groups and of alcohol acceptors were used to determine the versatility of these promoters. Disaccharide formation was demonstrated. In most cases, the In(III) compounds were shown to promote glycosylation better than the widely used promoter BF3 center dot OEt2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.10.016