5-酮果糖置于palladium Dihydroxide 氢气,Sodium Cyanoborohydride,溶剂黄146体系中,用 甲醇 作为反应溶剂,化学反应 6.0H,反应生成 Alpha-葡萄糖苷酶
参考文献:Expeditious Synthesis Of Aza Sugars By The Double Reductive Amination Of Dicarbonyl Sugars
标题:Expeditious Synthesis Of Aza Sugars By The Double Reductive Amination Of Dicarbonyl Sugars
摘要:Polyhydroxylated Pyrrolidines And Piperidines Were Prepared By The Double Reductive Amination Of Dicarbonyl,Sugars With Primary Amines And Nacnbh3 In Meoh. Stereocontrol In These Reactions Depended On The Nature Of The Amine And Dicarbonyl Sugar. For Example,5-Keto-D-Fructose (7) Gave Three Pyrrolidine Stereoisomers,With The N-Alkylated 2,5-Anhydro-2,5-Imino-D-Glucitol Predominating. Under Similar Reaction Conditions With Benzhydrylamine,5-Keto-D-Glucose (20) Afforded A 96:4 Mixture Of Piperidines Favoring D-Gluco 25A,Whereas 5-Keto-D-Mannose (6) Produced A 67:33 Mixture Enriched In D-Manno Isomer 40. This Method Allowed For The Direct And Relatively Short Synthesis Of 1-Deoxynojirimycin (Dnj,1) And 1-Deoxymannojirimycin (Dmj,5) And N-Alkylated Derivatives Thereof. Similar Reactions With O-Protected 5-Keto-D-Glucose Derivatives 21 And 22 Were Less Stereoselective And Lower Yielding.
DOI:10.1021/jo00090A040