4'-methoxyphenyl 1,3,4,5-tetra-O-benzoyl-β-D-fructopyranoside | 1418011-90-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-methoxyphenyl 1,3,4,5-tetra-O-benzoyl-β-D-fructopyranoside
• 英文别名: 4’-methoxyphenyl-1,3,4,5-tetra-O-benzoyl-β-D-fructopyranoside；[(2S,3S,4R,5R)-3,4,5-tribenzoyloxy-2-(4-methoxyphenoxy)oxan-2-yl]methyl benzoate
• CAS: 1418011-90-1
• 化学式: C₄₁H₃₄O₁₁
• 分子量: 702.714
• InChiKey: GPHIFGUMQMRALW-JAJQIJGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  1,3,4,5-tetra-O-benzoyl-β-D-fructopyranoside 在 三氟甲磺酸三甲基硅酯 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.5h， 生成 4'-methoxyphenyl 1,3,4,5-tetra-O-benzoyl-β-D-fructopyranoside
  参考文献：
  名称：

  Synthesis of β-d-fructopyranosides with N-phenyl trifluoroacetimidate donor

  摘要：

  Fructopyranosyl N-phenyl trifluoroacetimidate was demonstrated to be effective glycosyl donor for beta-D-fructopyranosides preparation that exhibited good beta-selectivity and good yields. X-ray data of two beta-D-fructopyranosides were obtained and help to determine the anomeric configuration of these ketoses. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.058

文献信息

• Synthesis of d-fructopyranosides with 2-O-acyl-β-d-fructopyranosides
  作者：Feng Lin、Qiulong Xu、Rui Lu、Liqun Yue

  DOI：10.1016/j.tetlet.2013.10.128

  日期：2014.1

  Glycosylation of 2-O-acyl fructopyranosides was investigated, which were shown to be effective glycosyl donors for D-fructopyranoside synthesis with good beta-selectivity and yields. For bulky acceptor 4e, alpha-anomer 5e was obtained with alpha/beta = 65:23. Unexpected ring-opening was observed during acetylation of 9, indicating the sensitivity of the fructopyranosyl ring. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of β-d-fructopyranosides with N-phenyl trifluoroacetimidate donor
  作者：Feng Lin、Gaoyan Lian、Qiulong Xu、Xiaofeng Zhu

  DOI：10.1016/j.tet.2012.11.058

  日期：2013.1

  Fructopyranosyl N-phenyl trifluoroacetimidate was demonstrated to be effective glycosyl donor for beta-D-fructopyranosides preparation that exhibited good beta-selectivity and good yields. X-ray data of two beta-D-fructopyranosides were obtained and help to determine the anomeric configuration of these ketoses. (C) 2012 Elsevier Ltd. All rights reserved.