3,4,6-Tri-O-acetyl-2-desoxy-α-D-arabino-hexopyranosyliodid | 75788-43-1

• 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: 3,4,6-Tri-O-acetyl-2-desoxy-α-D-arabino-hexopyranosyliodid
• 英文别名: 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-pyranosyl iodide；[(2R,3S,4R,6R)-3,4-diacetyloxy-6-iodooxan-2-yl]methyl acetate
• CAS: 75788-43-1
• 化学式: C₁₂H₁₇IO₇
• 分子量: 400.167
• InChiKey: FFNKKJQAISUYAY-WYUUTHIRSA-N

物化性质

• 沸点：
  405.6±45.0 °C(predicted)
• 密度：
  1.62±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  邻甲酚 、 3,4,6-Tri-O-acetyl-2-desoxy-α-D-arabino-hexopyranosyliodid 在 18-冠醚-6 、 4 A molecular sieve 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.42h， 以86%的产率得到o-cresyl 2-deoxy-3,4,6-tri-O-acetyl-β-D-arabino-pyranoside
  参考文献：
  名称：

  Efficient Route to 2-Deoxy β-O-Aryl-d-Glycosides via Direct Displacement of Glycosyl Iodides

  摘要：

  The conversion of glycals to 2-deoxy glycosyl acetates followed by reaction with trimethylsilyl iodide affords the corresponding glycosyl iodides, which readily undergo substitution with aryl alkoxy anions to provide 2-deoxy-beta-O-aryl glycosides. Direct displacement of the anomeric iodide alleviates the need to introduce temporary C-2 stereodirecting groups that require subsequent removal. The only observable byproducts from the glycosylations result from elimination of HI giving the starting glycals, which can be recycled through the reaction sequence.

  DOI：

  10.1021/ol035705v
• 作为产物：
  描述：

  1,3,4,6-O-四乙酰基-2-脱氧-D-吡喃葡萄糖 在 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 3,4,6-Tri-O-acetyl-2-desoxy-α-D-arabino-hexopyranosyliodid
  参考文献：
  名称：

  Efficient Route to 2-Deoxy β-O-Aryl-d-Glycosides via Direct Displacement of Glycosyl Iodides

  摘要：

  The conversion of glycals to 2-deoxy glycosyl acetates followed by reaction with trimethylsilyl iodide affords the corresponding glycosyl iodides, which readily undergo substitution with aryl alkoxy anions to provide 2-deoxy-beta-O-aryl glycosides. Direct displacement of the anomeric iodide alleviates the need to introduce temporary C-2 stereodirecting groups that require subsequent removal. The only observable byproducts from the glycosylations result from elimination of HI giving the starting glycals, which can be recycled through the reaction sequence.

  DOI：

  10.1021/ol035705v

文献信息

• Thiem, Joachim; Meyer, Bernd, Chemische Berichte, 1980, vol. 113, # 9, p. 3075 - 3085
  作者：Thiem, Joachim、Meyer, Bernd

  DOI：——

  日期：——