3,4-二-O-乙酰基-D-鼠李糖的合成

Synthesis of 3,4-Di-O-acetyl-D-rhamnal

标题化合物作为一种重要的有机合成中间体,在有机合成活性较高的天然产物中具有重要意义。以三-O-乙酰基-D-己烯糖作为起始原料,经脱乙酰基反应、磺酰化反应、乙酰化反应、亲核取代反应和还原反应合成目标产物。其中间体及目标产物的结构均经IR、~1HNMR和MS进行表征。对提高目标产物收率进行深入探索,结果表明,适当的反应时间、温度及投料的物质的量比分别能够有效提高乙酰化反应、亲核取代反应和还原反应的产品收率,总收率为63%。

The title compound is an important organic synthetic intermediate in synthesizing highly active natural products.Using tri-O-acetyl-D-glucal as starting material,the target product was synthesized by deacetylation,sulfonylation,acylation,nucleophilic substitution and reduction reaction.The structures of the intermediates and product were confirmed by IR,~1HNMR and MS.In order to improve the yield of the target product,the results show that the appropriate reaction time,temperature,and ratio of material mass can effectively improve the product yield of the acetylation reaction,nucleophilic substitution reaction,and reduction reaction,and the total yield is 63%.