(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 | 485802-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• CAS: 485802-74-2
• 化学式: C₂₃H₄₄O₁₄S₂Si
• 分子量: 636.811
• InChiKey: LEZRIYLZUQTWEN-ACBNXAFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.78
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  239.22
• 氢给体数：
  10.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (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 以 吡啶 为溶剂， 反应 4.0h， 生成
  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：

  2-(trimethylsilyl)ethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside 在 咪唑 、 碘 、 sodium methylate 、 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.0h， 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