S-(2,3,4,6-tetra-O-acetyl-glucopyranosyl)-(1->6)-S-2,3,4-tri-O-acetyl-1-S-acetyl-1,6-dithio-β-D-glucopyranose | 485802-70-8

• 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: S-(2,3,4,6-tetra-O-acetyl-glucopyranosyl)-(1->6)-S-2,3,4-tri-O-acetyl-1-S-acetyl-1,6-dithio-β-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-acetylsulfanyloxan-2-yl]methylsulfanyl]oxan-2-yl]methyl acetate
• CAS: 485802-70-8
• 化学式: C₂₈H₃₈O₁₇S₂
• 分子量: 710.732
• InChiKey: AJGMMKIYDUKTBP-AXXYRMHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  270
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  S-(2,3,4,6-tetra-O-acetyl-glucopyranosyl)-(1->6)-S-2,3,4-tri-O-acetyl-1-S-acetyl-1,6-dithio-β-D-glucopyranose 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-((((2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-((((2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-2-yl)methyl)thio)tetrahydro-2H-pyran-2-yl)methyl)thio)tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Synthesis of Novel Cyclic Oligosaccharides:  β-1,6-Thio-Linked Cycloglucopyranosides

  摘要：

  [GRAPHICS]A protocol for the synthesis of novel cyclic beta-1,6-S-linked glucopyranosides is developed. The key intermediate is a linear thiooligosaccharide bearing an iodo group at C-6 of the nonreducing sugar and a thioacetyl group at the anomeric center of the reducing end sugar. The crucial macrocyclization step was achieved through base-promoted intramolecular S(N)2 glycosylation in remarkably high yields (92-95%) and with well-controlled stereochemistry.

  DOI：

  10.1021/ol0270430
• 作为产物：
  描述：

  [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2S,3S,4S,5R)-3,4,5,6-tetraacetyloxyoxan-2-yl]methylsulfanyl]oxan-2-yl]methyl acetate 在 氢溴酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.75h， 生成 S-(2,3,4,6-tetra-O-acetyl-glucopyranosyl)-(1->6)-S-2,3,4-tri-O-acetyl-1-S-acetyl-1,6-dithio-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of Novel Cyclic Oligosaccharides:  β-1,6-Thio-Linked Cycloglucopyranosides

  摘要：

  [GRAPHICS]A protocol for the synthesis of novel cyclic beta-1,6-S-linked glucopyranosides is developed. The key intermediate is a linear thiooligosaccharide bearing an iodo group at C-6 of the nonreducing sugar and a thioacetyl group at the anomeric center of the reducing end sugar. The crucial macrocyclization step was achieved through base-promoted intramolecular S(N)2 glycosylation in remarkably high yields (92-95%) and with well-controlled stereochemistry.

  DOI：

  10.1021/ol0270430