以2,3,4,6-四-O-苄基-α-D-葡萄糖为原料,经4步反应制得中间体2,3,4,6-四-O-苄基-D-葡萄糖酸-δ-内酰胺(6);在碱性条件下6与正溴丁烷进行氮原子上的烃基化反应得N-丁基-2,3,4,6-四-O-苄基-D-葡萄糖酸-δ-内酰胺(7);用氢化铝锂将7的羰基还原为亚甲基得N-丁基-2,3,4,6-四-O-苄基-1-脱氧野尻霉素(8);8经催化氢解脱去苄基合成了N-丁基-1-脱氧野尻霉素,其结构经1H NMR,13C NMR和MS确证。
A new method for synthesizing N-butyl-1-deoxynojirmycin( 1) was reported. 2,3,4,6-Tetra-O-benzyl-D-glucono-δ-lactam( 6) was synthesized from 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose by a four-step reaction. Then,a butyl group was intruducted to 6 by N-alkylation reaction of the lactam with n-butyl bromide in the presence of bases. The N-butyl lactam was reduced to generate 2,3, 4,6-tetra-O-benzyl-N-butyl-1-deoxynojirmycin( 8) with lithium aluminum hydride as reducing agent. Finally,1 was obtained by the catalytic hydrogenolysis of 8 to remove benzyl group. The structures were confirmed by1H NMR,13C NMR and MS.