2-(trimethylsilyl)ethyl 2,3,4-tri-O-acetyl-6-O-deoxy-6-iodo-β-D-glucopyranside | 485802-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3,4-tri-O-acetyl-6-O-deoxy-6-iodo-β-D-glucopyranside
• 英文别名: [(2S,3S,4S,5R,6R)-4,5-diacetyloxy-2-(iodomethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl] acetate
• CAS: 485802-66-2
• 化学式: C₁₇H₂₉IO₈Si
• 分子量: 516.402
• InChiKey: SIFBHOVPFHGIPP-NQNKBUKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,4-tri-O-acetyl-6-O-deoxy-6-iodo-β-D-glucopyranside 在 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2S,3S,4S,5R)-3,4,5-triacetyloxy-6-hydroxyoxan-2-yl]methylsulfanyl]oxan-2-yl]methyl acetate
  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 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以95%的产率得到2-(trimethylsilyl)ethyl 2,3,4-tri-O-acetyl-6-O-deoxy-6-iodo-β-D-glucopyranside
  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