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,C14H18Cl3NO8,434.6605,(2S,3R,4R,5S,6S)-4,5-bis(acetyloxy)-6

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摘 要:,C14H18Cl3NO8,434.6605,(2S,3R,4R,5S,6S)-4,5-bis(acetyloxy)-6-methyl-2-[(2,2,2-trichloroethanimidoyl)oxy]tetrahydro-2H-pyran-3-yl acetate
  • 【化学名】(2S,3R,4R,5S,6S)-4,5-bis(acetyloxy)-6-methyl-2-[(2,2,2-trichloroethanimidoyl)oxy]tetrahydro-2H-pyran-3-yl acetate
  • 【CAS登记号】
  • 【结构式】,C14H18Cl3NO8,434.6605,(2S,3R,4R,5S,6S)-4,5-bis(acetyloxy)-6--药物合成数据库
  • 【分子式】C14H18Cl3NO8
  • 【分子量】434.6605
  • 【来源】
  • 【合成情况】 
  • 〖目标产物〗Dioscin
  • 〖合成路线〗
  • 〖合成方法〗The selective silylation of the primary OH group of (X) by means of Tbdms-Cl and imidazole gives the silyl ether (XI), which is condensed with 2,3,4-tri-O-acetyl-alpha-L-rahmnopyranosyl trichloroacetimidate (XII) by means of BF3/Et2O in dichloromethane to provide the protected diosgenyl trisaccharide (XIII). The desilylation of (XIII) by means of TBAF in THF gives the intermediate (XIV), which is finally fully deacylated by means of MeONa in MeOH/dichloromethane to afford the target diosgenyl trisaccharide.
  • 〖参考〗Zou, C.-C.; Hou, S.-J.; Shi, Y.; Lei, P.-S.; Liang, X.-T.; The synthesis of gracillin and dioscin: Two typical representatives of spirostanol glycosides. Carbohydr Res 2003, 338, 8, 721
 
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