2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-6-O-trifluoroethylsulfonato-α-D-glucopyranosyl-(1-6)-1.2:3.4-di-O-isopropylidene-α-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-6-O-trifluoroethylsulfonato-α-D-glucopyranosyl-(1-6)-1.2:3.4-di-O-isopropylidene-α-D-galactopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-5-azido-3-[(4-methoxyphenyl)methoxy]-4-phenylmethoxy-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-2-yl]methyl 2,2,2-trifluoroethyl sulfate
• 化学式: C₃₅H₄₄F₃N₃O₁₄S
• 分子量: 819.807
• InChiKey: RJBNSPGLVJHRIH-WKILFLJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  168
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside 在 molecular sieve 、 硼烷四氢呋喃络合物 、 diphenylboryl triflate 、 三氟甲磺酸酐 、 二苯基亚砜 、 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 2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-6-O-trifluoroethylsulfonato-α-D-glucopyranosyl-(1-6)-1.2:3.4-di-O-isopropylidene-α-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.