p-methoxyphenyl (3-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-trifluoroethylsulfonato-β-D-glucopyranosyluryl)-(1-4)-2-azido-3-O-benzoyl-6-O-benzyl-2-deoxy-4-O-trifluoroethylsulfonato-β-D-galactopyranoside | 763129-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl (3-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-trifluoroethylsulfonato-β-D-glucopyranosyluryl)-(1-4)-2-azido-3-O-benzoyl-6-O-benzyl-2-deoxy-4-O-trifluoroethylsulfonato-β-D-galactopyranoside
• 英文别名: [(2S,3R,4R,5R,6R)-3-azido-2-[(2R,3R,4S,5R,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(4-methoxyphenoxy)-4-phenylmethoxy-5-(2,2,2-trifluoroethoxysulfonyloxy)oxan-3-yl]oxy-6-(phenylmethoxymethyl)-5-(2,2,2-trifluoroethoxysulfonyloxy)oxan-4-yl] benzoate
• CAS: 763129-88-0
• 化学式: C₅₀H₅₉F₆N₃O₁₈S₂Si
• 分子量: 1196.24
• InChiKey: SHRAEGUBRYYBMI-GNUQTHRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.06
• 重原子数：
  80
• 可旋转键数：
  28
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl (3-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-trifluoroethylsulfonato-β-D-glucopyranosyluryl)-(1-4)-2-azido-3-O-benzoyl-6-O-benzyl-2-deoxy-4-O-trifluoroethylsulfonato-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以90%的产率得到p-methoxyphenyl (3-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-trifluoroethylsulfonato-β-D-glucopyranosyluryl)-(1-4)-2-azido-6-O-benzyl-2-deoxy-4-O-sulfonato-β-D-galactopyranoside
  参考文献：
  名称：

  Trifluoroethylsulfonate protected monosaccharides in glycosylation reactions

  摘要：

  A variety of sulfo-protected monosaccharide donors and acceptors were investigated in glycosylation reactions. Trifluoro-ethylsulfonate (SO3TFE) group was compatible with a wide range of activation conditions commonly used with fluoride, imidate, and sulfide donors. In addition, the influence of a SO3TFE group, at the critical 2-position in glycosyl donor, on the stereoselectivity of the glycosylation reaction was studied. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.131
• 作为产物：
  描述：

  4-甲氧苯基-3-O-苄基-4,6-O-苯亚甲基-β-D-吡喃葡萄糖苷 在 三氟化硼乙醚 、 三甲基铵三氧化硫共聚物 、 对甲苯磺酸 、 乙硫醇 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 105.5h， 生成 p-methoxyphenyl (3-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-trifluoroethylsulfonato-β-D-glucopyranosyluryl)-(1-4)-2-azido-3-O-benzoyl-6-O-benzyl-2-deoxy-4-O-trifluoroethylsulfonato-β-D-galactopyranoside
  参考文献：
  名称：

  Trifluoroethylsulfonate protected monosaccharides in glycosylation reactions

  摘要：

  A variety of sulfo-protected monosaccharide donors and acceptors were investigated in glycosylation reactions. Trifluoro-ethylsulfonate (SO3TFE) group was compatible with a wide range of activation conditions commonly used with fluoride, imidate, and sulfide donors. In addition, the influence of a SO3TFE group, at the critical 2-position in glycosyl donor, on the stereoselectivity of the glycosylation reaction was studied. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.131

文献信息

• Trifluoroethylsulfonate protected monosaccharides in glycosylation reactions
  作者：Nathalie A. Karst、Tasneem F. Islam、Fikri Y. Avci、Robert J. Linhardt

  DOI：10.1016/j.tetlet.2004.06.131

  日期：2004.8

  A variety of sulfo-protected monosaccharide donors and acceptors were investigated in glycosylation reactions. Trifluoro-ethylsulfonate (SO3TFE) group was compatible with a wide range of activation conditions commonly used with fluoride, imidate, and sulfide donors. In addition, the influence of a SO3TFE group, at the critical 2-position in glycosyl donor, on the stereoselectivity of the glycosylation reaction was studied. (C) 2004 Elsevier Ltd. All rights reserved.