6-O-acetyl-3,4-O-benzyl-2-O-trifluoroethylsulfonato-1-O-trichloroacetimidoyl-α-D-glucopyranoside | 763129-79-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-acetyl-3,4-O-benzyl-2-O-trifluoroethylsulfonato-1-O-trichloroacetimidoyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4-bis(phenylmethoxy)-6-(2,2,2-trichloroethanimidoyl)oxy-5-(2,2,2-trifluoroethoxysulfonyloxy)oxan-2-yl]methyl acetate
• CAS: 763129-79-9
• 化学式: C₂₆H₂₇Cl₃F₃NO₁₀S
• 分子量: 708.921
• InChiKey: LQEGRWUYQWQITQ-XNBWIAOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  双丙酮半乳糖 、 6-O-acetyl-3,4-O-benzyl-2-O-trifluoroethylsulfonato-1-O-trichloroacetimidoyl-α-D-glucopyranoside 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以66%的产率得到6-O-acetyl-3,4-O-benzyl-2-O-trifluoroethylsulfonato-α-D-glucopyranosyl-(1-6)-1.2:3.4-di-O-isopropylidene-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
• 作为产物：
  描述：

  p-methoxypheyl 3-O-benzyl-4,6-O-benzylidene-2-O-trifluoroethylsulfonato-β-D-glucopyranoside 在 硼烷四氢呋喃络合物 、 ammonium cerium(IV) nitrate 、 三氟甲磺酸二丁硼 作用下， 以 吡啶 、 水 、 甲苯 、 乙腈 为溶剂， 反应 5.5h， 生成 6-O-acetyl-3,4-O-benzyl-2-O-trifluoroethylsulfonato-1-O-trichloroacetimidoyl-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