Benzoic acid (2R,3R,4R,5R,6R)-3-azido-5-benzyloxy-2-fluoro-6-(2,2,2-trifluoro-ethoxysulfonyloxymethyl)-tetrahydro-pyran-4-yl ester | 640273-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid (2R,3R,4R,5R,6R)-3-azido-5-benzyloxy-2-fluoro-6-(2,2,2-trifluoro-ethoxysulfonyloxymethyl)-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4R,5R,6R)-3-azido-2-fluoro-5-phenylmethoxy-6-(2,2,2-trifluoroethoxysulfonyloxymethyl)oxan-4-yl] benzoate
• CAS: 640273-64-9
• 化学式: C₂₂H₂₁F₄N₃O₈S
• 分子量: 563.484
• InChiKey: XYGPWNCSCKDUIV-OBKDMQGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  双丙酮半乳糖 、 Benzoic acid (2R,3R,4R,5R,6R)-3-azido-5-benzyloxy-2-fluoro-6-(2,2,2-trifluoro-ethoxysulfonyloxymethyl)-tetrahydro-pyran-4-yl ester 在 二氯二茂锆 、 silver perchlorate 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到Benzoic acid (3R,4R,5R,6R)-3-azido-5-benzyloxy-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-6-(2,2,2-trifluoro-ethoxysulfonyloxymethyl)-tetrahydro-pyran-4-yl ester
  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：

  thexyldimethylsilyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 在 吡啶 、 三乙基硅烷 、 4 A molecular sieve 、 triethylamine trihydrofluoride 、 二氯苯酚溴酯 、 三甲基铵三氧化硫共聚物 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 、 柠檬酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 Benzoic acid (2R,3R,4R,5R,6R)-3-azido-5-benzyloxy-2-fluoro-6-(2,2,2-trifluoro-ethoxysulfonyloxymethyl)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Sulfo-Protected Hexosamine Monosaccharides:  Potentially Versatile Building Blocks for Glycosaminoglycan Synthesis

  摘要：

  [GRAPHICS]2,2,2-Trifluorodiazoethane was investigated as a reagent for sulfo group protection on hexosamine monosaccharides. The synthesis of glucosamine and galactosamine building blocks fully differentiated for glycosaminoglycan synthesis and the synthesis of glycosyl donors are described. The compatibility of trifluoroethylsulfonate under a variety of reaction conditions has also been investigated.

  DOI：

  10.1021/ol035882w

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.
• Sulfo-Protected Hexosamine Monosaccharides:  Potentially Versatile Building Blocks for Glycosaminoglycan Synthesis
  作者：Nathalie A. Karst、Tasneem F. Islam、Robert J. Linhardt

  DOI：10.1021/ol035882w

  日期：2003.12.1

  [GRAPHICS]2,2,2-Trifluorodiazoethane was investigated as a reagent for sulfo group protection on hexosamine monosaccharides. The synthesis of glucosamine and galactosamine building blocks fully differentiated for glycosaminoglycan synthesis and the synthesis of glycosyl donors are described. The compatibility of trifluoroethylsulfonate under a variety of reaction conditions has also been investigated.