p-methoxyphenyl 3-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-trifluoroethylsulfonato-β-D-glucopyranoside | 763129-84-6

• 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-glucopyranoside
• 英文别名: [(2S,3R,4S,5R,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-hydroxy-2-(4-methoxyphenoxy)-4-phenylmethoxyoxan-3-yl] 2,2,2-trifluoroethyl sulfate
• CAS: 763129-84-6
• 化学式: C₂₈H₃₉F₃O₁₀SSi
• 分子量: 652.758
• InChiKey: XXYDTYPKZORDRB-WSGIOKLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  13

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-glucopyranoside 在 三氟化硼乙醚 、 potassium tert-butylate 、 sodium methylate 作用下， 以 甲醇 、 甲苯 、 叔丁醇 为溶剂， 反应 44.0h， 生成 p-methoxyphenyl (3-O-benzyl-2-O-sulfonato-β-D-glucopyranosyl)-(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 为溶剂， 反应 97.5h， 生成 p-methoxyphenyl 3-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-trifluoroethylsulfonato-β-D-glucopyranoside
  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.