Benzoic acid (2S,3R,4R,5R,6R)-3-azido-5-benzyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-hydroxymethyl-tetrahydro-pyran-4-yl ester | 640273-70-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoic acid (2S,3R,4R,5R,6R)-3-azido-5-benzyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-hydroxymethyl-tetrahydro-pyran-4-yl ester
• 英文别名: [(2S,3R,4R,5R,6R)-3-azido-2-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-6-(hydroxymethyl)-5-phenylmethoxyoxan-4-yl] benzoate
• CAS: 640273-70-7
• 化学式: C₂₈H₃₉N₃O₆Si
• 分子量: 541.72
• InChiKey: OUZLVNUGKGUJNM-NUPXYHBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  88.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2S,3R,4R,5R,6R)-3-azido-5-benzyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-hydroxymethyl-tetrahydro-pyran-4-yl ester 在 三甲基铵三氧化硫共聚物 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Benzoic acid (2S,3R,4R,5R,6R)-3-azido-5-benzyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-sulfooxymethyl-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
• 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 、 二氯苯酚溴酯 作用下， 以 二氯甲烷 为溶剂， 生成 Benzoic acid (2S,3R,4R,5R,6R)-3-azido-5-benzyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-hydroxymethyl-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

• 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.