1,3,6-tri-O-acetyl-2-C-[6-O-acetyl-2,3-dideoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-erythro-hex-2-enopyranosyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-deoxy-α-D-glucopyranose | 476460-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,6-tri-O-acetyl-2-C-[6-O-acetyl-2,3-dideoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-erythro-hex-2-enopyranosyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-deoxy-α-D-glucopyranose
• 英文别名: [(2R,3S,6S)-6-[(2R,3R,4R,5S,6R)-2,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-3-yl]-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 476460-77-2
• 化学式: C₄₈H₆₄O₃₀
• 分子量: 1121.02
• InChiKey: FCRQYSCGHJKCDT-FEBSWZKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  78
• 可旋转键数：
  33
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  371
• 氢给体数：
  0
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  1,3,6-tri-O-acetyl-2-C-[6-O-acetyl-2,3-dideoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-erythro-hex-2-enopyranosyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-deoxy-α-D-glucopyranose 、 三甲基氰硅烷 在 氰化汞 、 mercury dibromide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 24.0h， 以52%的产率得到3,6-di-O-acetyl-2-C-[6-O-acetyl-2,3-dideoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-erythro-hex-2-enopyranosyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1,2-dideoxy-α-D-glucopyranosyl cyanide
  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：

  4-O-(2,3,4,6-四-O-乙酰基)-β-D-吡喃(型)葡糖基-D-吡喃(型)葡糖四乙酸酯 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 1,3,6-tri-O-acetyl-2-C-[6-O-acetyl-2,3-dideoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-erythro-hex-2-enopyranosyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-deoxy-α-D-glucopyranose
  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