p-tolyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside | 1320281-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: p-tolyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside
• 英文别名: tolyl 2-azido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside
• CAS: 1320281-36-4
• 化学式: C₂₇H₂₇N₃O₄S
• 分子量: 489.595
• InChiKey: LSFXJSWSDKKNNC-HXPCJYLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  85.68
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 p-tolyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside 、 methyl (p-tolyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosyluronate) 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-(methyl 4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-β-D-mannopyranosyluronate)-α-D-glucopyranoside 、 methyl 2,3,4-tri-O-benzyl-6-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α,β-D-mannopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Mannopyranosyl Uronic Acid Donor Reactivity

  摘要：

  The reactivity of a variety of mannopyranosyl uronic acid donors was assessed In a set of competition experiments, in which two (S)-tolyl mannosyl donors were made to compete for a limited amount of promoter (NIS/TfOH). These experiments revealed that the reactivity of mannuronic acid donors is significantly higher than expected based on the electron-withdrawing capacity of the C-5 carboxylic acid ester function. A 4-O-acetyl-beta-(S)-tolyl mannuronic acid donor was found to have similar reactivity as per-O-benzyl-alpha-(S)-tolyl mannose.

  DOI：

  10.1021/ol2016862
• 作为产物：
  描述：

  acetyl 4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-mannopyranoside 在 甲醇 、 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 作用下， 以 1,1-二氯乙烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 98.0h， 生成 p-tolyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Mannopyranosyl Uronic Acid Donor Reactivity

  摘要：

  The reactivity of a variety of mannopyranosyl uronic acid donors was assessed In a set of competition experiments, in which two (S)-tolyl mannosyl donors were made to compete for a limited amount of promoter (NIS/TfOH). These experiments revealed that the reactivity of mannuronic acid donors is significantly higher than expected based on the electron-withdrawing capacity of the C-5 carboxylic acid ester function. A 4-O-acetyl-beta-(S)-tolyl mannuronic acid donor was found to have similar reactivity as per-O-benzyl-alpha-(S)-tolyl mannose.

  DOI：

  10.1021/ol2016862

文献信息

• Rate-Dependent Inverse-Addition β-Selective Mannosylation and Contiguous Sequential Glycosylation Involving β-Mannosidic Bond Formation
  作者：Shih-Sheng Chang、Che-Hao Shih、Kwun-Cheng Lai、Kwok-Kong Tony Mong

  DOI：10.1002/asia.200900765

  日期：2010.5.3

  development of the contiguous sequential glycosylation strategy, which streamlines the preparation of oligosaccharides invoking β‐mannosidic bond formation. The synthetic utility of the contiguous glycosylation strategy was demonstrated by the preparation of the trisaccharide core of human N‐linked glycoproteins and the trisaccharide repeating unit of the O‐specific polysaccharide found in the cellular capsule

  已发现甘露糖基化反应的β选择性取决于反向加成（I-A）程序中甘露糖基三氯乙酰亚氨酸酯供体的添加速率。这种依赖于速率的I‐A程序可以改善直接β-甘露糖基化的选择性，并且适用于硫代糖苷受体的正交糖基化。对该新方法的进一步阐述使得能够开发出连续的顺序糖基化策略，从而简化了制备β-甘露糖苷键形成的寡糖的制备。通过制备人N连接糖蛋白的三糖核心和沙门氏菌细胞膜中发现的O特异性多糖的三糖重复单元，证明了连续糖基化策略的合成效用。