methyl [benzyl O-(2-azido-3-O-benzyl-2-deoxy-6-O-trifluoroethylsulfonato-α-D-glucopyranosyl)-(1-6)-2.3-di-O-benzoyl-β-D-glucopyranoside]uronate | 763129-87-9

• 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: methyl [benzyl O-(2-azido-3-O-benzyl-2-deoxy-6-O-trifluoroethylsulfonato-α-D-glucopyranosyl)-(1-6)-2.3-di-O-benzoyl-β-D-glucopyranoside]uronate
• 英文别名: methyl (2S,3S,4S,5R,6R)-3-[(2R,3R,4R,5S,6R)-3-azido-5-hydroxy-4-phenylmethoxy-6-(2,2,2-trifluoroethoxysulfonyloxymethyl)oxan-2-yl]oxy-4,5-dibenzoyloxy-6-phenylmethoxyoxane-2-carboxylate
• CAS: 763129-87-9
• 化学式: C₄₃H₄₂F₃N₃O₁₆S
• 分子量: 945.878
• InChiKey: HSFWXNNAFIGRHP-NJXWIFHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  66
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  221
• 氢给体数：
  1
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  methyl [benzyl O-(2-azido-3-O-benzyl-2-deoxy-6-O-trifluoroethylsulfonato-α-D-glucopyranosyl)-(1-6)-2.3-di-O-benzoyl-β-D-glucopyranoside]uronate 在 sodium methylate 、 potassium tert-butylate 作用下， 以 甲醇 、 叔丁醇 为溶剂， 以60%的产率得到methyl [benzyl O-(2-azido-3-O-benzyl-2-deoxy-6-O-sulfonato-α-D-glucopyranosyl)-(1-4)-β-D-glucopyranoside]uronate
  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：

  苄基beta-D-吡喃葡糖苷酸甲酯三乙酸酯 在 二氯二茂锆 、 sodium methylate 、 silver perchlorate 、 二正丁基氧化锡 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl [benzyl O-(2-azido-3-O-benzyl-2-deoxy-6-O-trifluoroethylsulfonato-α-D-glucopyranosyl)-(1-6)-2.3-di-O-benzoyl-β-D-glucopyranoside]uronate
  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.