Acetic acid (2S,5R,6R,3'R,4'R,5'R,6'R)-5,2',5'-triacetoxy-6,6'-bis-acetoxymethyl-5,6,3',4',5',6'-hexahydro-2H,2'H-[2,3']bipyranyl-4'-yl ester | 476460-76-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2S,5R,6R,3'R,4'R,5'R,6'R)-5,2',5'-triacetoxy-6,6'-bis-acetoxymethyl-5,6,3',4',5',6'-hexahydro-2H,2'H-[2,3']bipyranyl-4'-yl ester
• 英文别名: [(2R,3R,6S)-3-acetyloxy-6-[(3R,4R,5R,6R)-2,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-3-yl]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 476460-76-1
• 化学式: C₂₄H₃₂O₁₄
• 分子量: 544.51
• InChiKey: GYHDLQWHVHJGME-JALILVTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  三甲基氰硅烷 、 Acetic acid (2S,5R,6R,3'R,4'R,5'R,6'R)-5,2',5'-triacetoxy-6,6'-bis-acetoxymethyl-5,6,3',4',5',6'-hexahydro-2H,2'H-[2,3']bipyranyl-4'-yl ester 在 氰化汞 、 mercury dibromide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 24.0h， 以79%的产率得到Acetic acid (2S,5R,6R,2'S,5'R,6'R)-5-acetoxy-6,6'-bis-acetoxymethyl-2'-cyano-5,6,5',6'-tetrahydro-2H,2'H-[2,3']bipyranyl-5'-yl ester
  参考文献：
  名称：

  Mild Synthesis of Disaccharidic 2,3-Enopyranosyl Cyanides and 2-C-2-Deoxy Pyranosyl Cyanides with Hg(CN)₂/HgBr₂/TMSCN

  摘要：

  Lewis acid-catalyzed dimerization of mono- and disaccharidic per-O-acetylated glycals gave di- and tetrasaccharidic O-acetylated C-glycosides, respectively. 2,3-Enopyranosyl cyanides were obtained from per-O-acetylated glycals by a new, mild anomeric S-N'-acetoxy displacement with Hg(CN)(2)/HgBr2/TMSCN. Per-O-acetylated 2-C-2-deoxy-pyranoses were converted into pyranosyl cyanides by the same reagent. An unprecedented acetic acid elimination from dimers with D-galacto- and L-fuco-configurations accompanied the S-N-displacement under those conditions. A new set of H-1 NMR coupling constants for 2,3-enopyranosyl systems was used for configurational assignment of complicated tetrasaccharide mimics.

  DOI：

  10.1021/jo0111661
• 作为产物：
  描述：

  1,2,3,4,6-D-葡萄糖五乙酸酯 在 N-甲基咪唑 、 4 A molecular sieve 、 三氟化硼乙醚 、 溴化钛(IV) 、 铜 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 36.25h， 生成 Acetic acid (2S,5R,6R,3'R,4'R,5'R,6'R)-5,2',5'-triacetoxy-6,6'-bis-acetoxymethyl-5,6,3',4',5',6'-hexahydro-2H,2'H-[2,3']bipyranyl-4'-yl ester
  参考文献：
  名称：

  Mild Synthesis of Disaccharidic 2,3-Enopyranosyl Cyanides and 2-C-2-Deoxy Pyranosyl Cyanides with Hg(CN)₂/HgBr₂/TMSCN

  摘要：

  Lewis acid-catalyzed dimerization of mono- and disaccharidic per-O-acetylated glycals gave di- and tetrasaccharidic O-acetylated C-glycosides, respectively. 2,3-Enopyranosyl cyanides were obtained from per-O-acetylated glycals by a new, mild anomeric S-N'-acetoxy displacement with Hg(CN)(2)/HgBr2/TMSCN. Per-O-acetylated 2-C-2-deoxy-pyranoses were converted into pyranosyl cyanides by the same reagent. An unprecedented acetic acid elimination from dimers with D-galacto- and L-fuco-configurations accompanied the S-N-displacement under those conditions. A new set of H-1 NMR coupling constants for 2,3-enopyranosyl systems was used for configurational assignment of complicated tetrasaccharide mimics.

  DOI：

  10.1021/jo0111661