(4aR,7S,8R,8aR)-7-Butyryloxy-8-hydroxy-2-phenyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid benzyl ester | 138309-87-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4aR,7S,8R,8aR)-7-Butyryloxy-8-hydroxy-2-phenyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid benzyl ester
• CAS: 138309-87-2
• 化学式: C₂₅H₂₉NO₇
• 分子量: 455.508
• InChiKey: YQJYLVLKFSSBGU-PGXMJIPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  94.53
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  苯甲醛 在 4 A molecular sieve 、 二正丁基氧化锡 、 三乙胺 、 zinc(II) chloride 作用下， 生成 (4aR,7S,8R,8aR)-7-Butyryloxy-8-hydroxy-2-phenyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid benzyl ester
  参考文献：
  名称：

  Selective functionalization of the C2 hydroxyl group of N-carbobenzyloxy-4,6--benzylidene-1-deoxynojirimycin

  摘要：

  1-Deoxynojirimycin was converted into its N-CBZ-4,6-O-benzylidene derivative 2 in two steps in 51% yield. Compound 2 could be regioselectively functionalized at the C2 hydroxyl group by activation with di-n-butyltin oxide, followed by reaction of the resulting stannylene with electrophiles. In this manner, the 2-O-benzoyl and 2-O-tosyl analogs could be obtained in yields of 73% and 94%, respectively.

  DOI：

  10.1016/s0040-4039(00)93531-7