2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose | 1447801-82-2

• 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: 2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose
• 英文别名: 1-O-tert-butyldimethylsilyl-3-O-benzyl-6-O-benzoyl-2-azido-2-deoxy-β-D-glucopyranose；[(2R,3S,4R,5R,6S)-5-azido-6-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-4-phenylmethoxyoxan-2-yl]methyl benzoate
• CAS: 1447801-82-2
• 化学式: C₂₆H₃₅N₃O₆Si
• 分子量: 513.666
• InChiKey: QKBRWZUGUFSWSG-GAQRMDFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-levuniloyl-α/β-D-glucopyranose
  参考文献：
  名称：

  Toward the Solid-Phase Synthesis of Heparan Sulfate Oligosaccharides: Evaluation of Iduronic Acid and Idose Building Blocks

  摘要：

  Glycan arrays have been established as the premier technical platform for assessing the specificity of carbohydrate binding proteins, an important step in functional glycomics research. Access to large libraries of well-characterized oligosaccharides remains a major bottleneck of glycan array research, and this is particularly true for glycosaminoglycans (GAGs), a class of linear sulfated polysaccharides which are present on most animal cells. Solid-supported synthesis is a potentially powerful tool for the accelerated synthesis of relevant GAG libraries with variations in glycan sequence and sulfation pattern. We have evaluated a series of iduronic acid and idose donors, including a couple of novel n-pentenyl orthoester donors in the sequential assembly of heparan sulfate precursors from monosaccharide building blocks in solution and on a polystyrene resin. The systematic study of donor and acceptor performance up to the trisaccharide stage in solution and on the solid support have resulted in a general strategy for the solid-phase assembly of this important class of glycans.

  DOI：

  10.1021/jo400467g
• 作为产物：
  描述：

  2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose 在 对甲苯磺酸 、 三乙胺 、 乙硫醇 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 14.0h， 生成 2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Toward the Solid-Phase Synthesis of Heparan Sulfate Oligosaccharides: Evaluation of Iduronic Acid and Idose Building Blocks

  摘要：

  Glycan arrays have been established as the premier technical platform for assessing the specificity of carbohydrate binding proteins, an important step in functional glycomics research. Access to large libraries of well-characterized oligosaccharides remains a major bottleneck of glycan array research, and this is particularly true for glycosaminoglycans (GAGs), a class of linear sulfated polysaccharides which are present on most animal cells. Solid-supported synthesis is a potentially powerful tool for the accelerated synthesis of relevant GAG libraries with variations in glycan sequence and sulfation pattern. We have evaluated a series of iduronic acid and idose donors, including a couple of novel n-pentenyl orthoester donors in the sequential assembly of heparan sulfate precursors from monosaccharide building blocks in solution and on a polystyrene resin. The systematic study of donor and acceptor performance up to the trisaccharide stage in solution and on the solid support have resulted in a general strategy for the solid-phase assembly of this important class of glycans.

  DOI：

  10.1021/jo400467g

文献信息

• More than a Leaving Group: <i>N</i> ‐Phenyltrifluoroacetimidate as a Remote Directing Group for Highly α‐Selective 1,2‐ <i>cis</i> Glycosylation
  作者：Xianglai Liu、Yingying Song、Ao Liu、Yueer Zhou、Qian Zhu、Yetong Lin、Huiyong Sun、Kaidi Zhu、Wei Liu、Ning Ding、Weijia Xie、Haopeng Sun、Biao Yu、Peng Xu、Wei Li

  DOI：10.1002/anie.202201510

  日期：2022.5.16

  An N-phenyltrifluoroacetimidoyl group at O6 was found to be highly stereodirecting for the challenging 1,2-cis α-glycosylation. Its remote participation is supported by characterization of the crucial 1,6-bridged bicyclic cation intermediates as well as other experimental evidence.

  发现 O6 处的N-苯基三氟乙亚氨基酰基对具有挑战性的 1,2-顺式α-糖基化具有高度立体定向性。它的远程参与得到了关键 1,6-桥双环阳离子中间体的表征以及其他实验证据的支持。