tert-butyl (3S,7R,7aS)-3-((2'S,3'S,4'R,5'R,6'R)-4',5'-bis(benzyloxy)-6'-(benzyloxymethyl)-3'-nitrotetrahydro-2'H-pyran-2'-yl)-7-methoxy-7,7a-dimethyl-5-oxotetrahydro-2H-oxazolo[3,2-c]oxazole-3-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl (3S,7R,7aS)-3-((2'S,3'S,4'R,5'R,6'R)-4',5'-bis(benzyloxy)-6'-(benzyloxymethyl)-3'-nitrotetrahydro-2'H-pyran-2'-yl)-7-methoxy-7,7a-dimethyl-5-oxotetrahydro-2H-oxazolo[3,2-c]oxazole-3-carboxylate
• 英文别名: tert-butyl (3R,7R,7aS)-7-methoxy-7,7a-dimethyl-3-[(2S,3S,4R,5R,6R)-3-nitro-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]-5-oxo-2H-[1,3]oxazolo[4,3-b][1,3]oxazole-3-carboxylate
• 化学式: C₄₀H₄₈N₂O₁₂
• 分子量: 748.827
• InChiKey: GYMOTTJUDKFMGX-LXRJSSBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  54
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  157
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (3S,7R,7aS)-tetrahydro-7-methoxy-7,7a-dimethyl-5-oxo-2H-oxazolo[3,2-c]oxazole-3-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 、 三甲基乙酸酐 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.08h， 生成 tert-butyl (3S,7R,7aS)-3-((2'S,3'S,4'R,5'R,6'R)-4',5'-bis(benzyloxy)-6'-(benzyloxymethyl)-3'-nitrotetrahydro-2'H-pyran-2'-yl)-7-methoxy-7,7a-dimethyl-5-oxotetrahydro-2H-oxazolo[3,2-c]oxazole-3-carboxylate
  参考文献：
  名称：

  A Double Diastereoselective Michael-Type Addition as an Entry to Conformationally Restricted Tn Antigen Mimics

  摘要：

  A totally stereocontrolled C-Michael addition of serine-equivalent C-nucleophiles to tri-O-benzyl-2-nitro-D-galactal was used as the key step to synthesize several pyrano[3,2-b]pyrrole structures. These scaffolds could be regarded as conformationally restricted Tn antigen mimics, as we have demonstrated by biological assays. The pyranose rings retain their C-4(1) chair conformation, as shown by molecular modeling and NMR spectroscopy. The expected bioactivity was established by a competition-tailored enzyme-linked lectin assay using both soybean and Vicia villosa agglutinins as model lectins. The facile described synthetic route and the strategic combination of computational and experimental techniques to reveal conformational features and bioactivity demonstrate the prepared glycomimics to be promising candidates for further exploitation of this scaffold to give glycans for lectin blocking and vaccination.

  DOI：

  10.1021/jo4019396

文献信息

• A Double Diastereoselective Michael-Type Addition as an Entry to Conformationally Restricted Tn Antigen Mimics
  作者：Carlos Aydillo、Claudio D. Navo、Jesús H. Busto、Francisco Corzana、María M. Zurbano、Alberto Avenoza、Jesús M. Peregrina

  DOI：10.1021/jo4019396

  日期：2013.11.1

  A totally stereocontrolled C-Michael addition of serine-equivalent C-nucleophiles to tri-O-benzyl-2-nitro-D-galactal was used as the key step to synthesize several pyrano[3,2-b]pyrrole structures. These scaffolds could be regarded as conformationally restricted Tn antigen mimics, as we have demonstrated by biological assays. The pyranose rings retain their C-4(1) chair conformation, as shown by molecular modeling and NMR spectroscopy. The expected bioactivity was established by a competition-tailored enzyme-linked lectin assay using both soybean and Vicia villosa agglutinins as model lectins. The facile described synthetic route and the strategic combination of computational and experimental techniques to reveal conformational features and bioactivity demonstrate the prepared glycomimics to be promising candidates for further exploitation of this scaffold to give glycans for lectin blocking and vaccination.