methyl (2-C-(3,3-dimethyl-2-oxobutyl)-5-N-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranitol)onate | 1359855-62-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2-C-(3,3-dimethyl-2-oxobutyl)-5-N-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranitol)onate
• CAS: 1359855-62-1
• 化学式: C₁₈H₃₁NO₉
• 分子量: 405.445
• InChiKey: BCJCBPWCMUEPOE-ULPPIJFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.73
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  162.62
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  methyl (2-C-(3,3-dimethyl-2-oxobutyl)-5-N-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranitol)onate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.58h， 以100%的产率得到methyl (2-C-(3,3-dimethyl-2-oxobutyl)-5-N-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranitol)onate
  参考文献：
  名称：

  Stereoselective, Electrophilic α-C-Sialidation

  摘要：

  5-N-Acetyl-5-N,4-O-oxazolidinone protected alpha- and beta-sialyl phosphates react with allyltributylstannane and a variety of trimethylsilyl enol ethers to give alpha-sialyl C-glycosides in high yield and excellent selectivity. Elimination to give the 2,3-glycal is minimized by the presence of the oxazolidinone ring. The oxazolidinone ring can be subsequently cleaved under mild conditions at room temperature leaving in place the native acetamide group.

  DOI：

  10.1021/ol300255q