(6S,7R,8R,8aR)-8-(tert-Butyl-diphenyl-silanyloxy)-6,7-dihydroxy-hexahydro-oxazolo[3,4-a]pyridin-3-one | 203253-81-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (6S,7R,8R,8aR)-8-(tert-Butyl-diphenyl-silanyloxy)-6,7-dihydroxy-hexahydro-oxazolo[3,4-a]pyridin-3-one
• 英文别名: (6S,7R,8R,8aR)-8-[tert-butyl(diphenyl)silyl]oxy-6,7-dihydroxy-1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-3-one
• CAS: 203253-81-0
• 化学式: C₂₃H₂₉NO₅Si
• 分子量: 427.572
• InChiKey: RJRPWMIVEOZQFM-PLACYPQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6S,7R,8R,8aR)-8-(tert-Butyl-diphenyl-silanyloxy)-6,7-dihydroxy-hexahydro-oxazolo[3,4-a]pyridin-3-one 在 4-二甲氨基吡啶 、 sodium hydroxide 、 18-冠醚-6 、 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 28.0h， 生成 1-脱氧甘露伊霉素
  参考文献：
  名称：

  Chemical Transformation of a 1-Deoxynojirimycin Derivative into 1-Deoxymannojirimycin and 1-Deoxygalactostatin

  摘要：

  Treatment of 2,3-di-O-benzyl-N-benzyloxycarbonyl-6-O-t-butyldiphenylsilyl-1-5-dideoxy-1,5-imino-D-glucitol (4) with sodium hydride resulted in an intramolecular cyclization concomitant with silyl migration, giving the carbamate derivative 5 in good yield. This was efficiently converted into 1-deoxymannojirimycin (2) via regioselective p-toluenesulfonylation followed by an inversion reaction at the C-2 position. On the other hand, the monochloromethylsulfonate 10 obtained from 4 underwent configurational change at the C-4 position by the action of sodium benzoate. The resulting benzoate 11 was deprotected to afford 1-deoxygalactostatin (3).

  DOI：

  10.1080/07328309808005772
• 作为产物：
  描述：

  N-benzyloxycarbonyl-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-1,5-imino-D-gulcitol 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 水 、 溶剂黄146 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.08h， 生成 (6S,7R,8R,8aR)-8-(tert-Butyl-diphenyl-silanyloxy)-6,7-dihydroxy-hexahydro-oxazolo[3,4-a]pyridin-3-one
  参考文献：
  名称：

  Chemical Transformation of a 1-Deoxynojirimycin Derivative into 1-Deoxymannojirimycin and 1-Deoxygalactostatin

  摘要：

  Treatment of 2,3-di-O-benzyl-N-benzyloxycarbonyl-6-O-t-butyldiphenylsilyl-1-5-dideoxy-1,5-imino-D-glucitol (4) with sodium hydride resulted in an intramolecular cyclization concomitant with silyl migration, giving the carbamate derivative 5 in good yield. This was efficiently converted into 1-deoxymannojirimycin (2) via regioselective p-toluenesulfonylation followed by an inversion reaction at the C-2 position. On the other hand, the monochloromethylsulfonate 10 obtained from 4 underwent configurational change at the C-4 position by the action of sodium benzoate. The resulting benzoate 11 was deprotected to afford 1-deoxygalactostatin (3).

  DOI：

  10.1080/07328309808005772