2-O-Acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl N-methylimidazolyl sulfone | 197158-94-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-Acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl N-methylimidazolyl sulfone
• CAS: 197158-94-4
• 化学式: C₃₃H₃₆N₂O₈S
• 分子量: 620.723
• InChiKey: WHPVFRXUOQTHKY-DSSMMGBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  44.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  115.18
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-O-Acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl N-methylimidazolyl sulfone 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到3,4,6-三苄氧基-D-葡萄烯糖
  参考文献：
  名称：

  1,2-cis-C-glycoside synthesis by samarium diiodide-promoted radical cyclizations

  摘要：

  AbstractThe samarium diiodide reduction of glycosyl pyridyl sulfones bearing a silicon‐tethered unsaturated group at the C2–OH position leads to the stereo‐specific synthesis of 1,2‐cis‐C‐glycosides in good yield after desilylation. These reactions proceed via an anomeric radical with subsequent 5‐exo cyclization. Unlike the corresponding glycosyl phenyl sulfones, the pyridyl derivatives react instantaneously with samarium diiodide and do not require a cosolvent such as hexamethylphosphoramide (HMPA). Under these reaction conditions radical cyclization precedes the second reduction step. Examples of 5‐exo‐trig and ‐dig ring closures are given. The synthetic utility of this method was demonstrated by a short synthesis of methyl C‐isomaltoside.

  DOI：

  10.1002/chem.19970030822
• 作为产物：
  描述：

  3,4,6-三-O-苄基-beta-D-吡喃甘露糖-1,2-(甲基原乙酸酯) 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 15.0h， 生成 2-O-Acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl N-methylimidazolyl sulfone
  参考文献：
  名称：

  1,2-cis-C-glycoside synthesis by samarium diiodide-promoted radical cyclizations

  摘要：

  AbstractThe samarium diiodide reduction of glycosyl pyridyl sulfones bearing a silicon‐tethered unsaturated group at the C2–OH position leads to the stereo‐specific synthesis of 1,2‐cis‐C‐glycosides in good yield after desilylation. These reactions proceed via an anomeric radical with subsequent 5‐exo cyclization. Unlike the corresponding glycosyl phenyl sulfones, the pyridyl derivatives react instantaneously with samarium diiodide and do not require a cosolvent such as hexamethylphosphoramide (HMPA). Under these reaction conditions radical cyclization precedes the second reduction step. Examples of 5‐exo‐trig and ‐dig ring closures are given. The synthetic utility of this method was demonstrated by a short synthesis of methyl C‐isomaltoside.

  DOI：

  10.1002/chem.19970030822