phenyl 2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-1-thio-6-O-trifluoroethylsulfonate-α-D-glucopyranoside | 763129-73-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-1-thio-6-O-trifluoroethylsulfonate-α-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-azido-3-[(4-methoxyphenyl)methoxy]-4-phenylmethoxy-6-phenylsulfanyloxan-2-yl]methyl 2,2,2-trifluoroethyl sulfate
• CAS: 763129-73-3
• 化学式: C₂₉H₃₀F₃N₃O₈S₂
• 分子量: 669.7
• InChiKey: AZHXHKSEMYMAIU-JQPIIJRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  phenyl 2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-1-thio-6-O-trifluoroethylsulfonate-α-D-glucopyranoside 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以86%的产率得到phenylsulfenyl 2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-6-O-trifluoroethylsulfonato-α-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
• 作为产物：
  描述：

  phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside 在 硼烷四氢呋喃络合物 、 diphenylboryl triflate 、 sodium methylate 、 三乙胺三氧化硫 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.84h， 生成 phenyl 2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-1-thio-6-O-trifluoroethylsulfonate-α-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.