以氧化糖为原料的氨基糖衍生物的合成

Synthesis of Aminosugars Having New Structures from Oxosugars

首次报道了以氧化糖为原料的氨基糖衍生物的合成方法.以2位氧化糖为原料与芳胺反应得到羰基转至3位的2位脱氧2位胺基糖,此胺基糖经NaBH_4立体选择性还原及AcOH脱去4,6位保护基,合成了新型的D-阿洛糖胺.X射线单晶衍射分析表明其晶体中有多种氢键,由于氢键作用,晶体呈现三维超分子结构.对2位氧化糖与H_2NC_6H_4COOEt反应生成α,β-不饱和酮糖的机理进行了探讨.以5位氧化糖为原料通过碳基转位反应合成了新型的二氢-1,4-苯并二嗪氨基糖.

A new method for synthesis of aminosugars having new structures from oxosugars was established for the first time. Stereoselective synthesis of D-allosamine from 2-oxoglucopyranoside was achieved via 'carbonyl group transfer reaction' followed by stereoselective reduction with NaBH4 and deprotection with 40% AcOH. X-Ray crystallographic analysis indicates that it has three dimensional supramolecular structure, which was formed by many hydrogen interactions. In addition, the mechanism of the formation of another aminosugar with a, P-unsaturated ketone structure by the reaction of 2-oxoglucopyranoside with H2NC6H4COOEt was explained. Dihydro-1, 4-benzodiazine aminosugar was also synthesized from 5-oxoglucofuranose by reacting with o-benzyldiamine via 'carbonyl group transfer reaction'.