1,2-缩水-3,4-二-O-苄基-6-脱氧-β-L-塔罗吡喃糖的合成

SYNTHESIS OF l,2-ANHYDRO-3,4-DI-O-BENZYL-6-DEOXY-0-L -TALOPYRANOSE

以L-鼠李糖为原料.首先合成(?)脱氧塔罗糖的衍生物(5),再经过一系列反应得到2-O-乙酸基-3,4-(?)-O-(?)基-6-脱氧-α-L-塔罗吡喃糖氯代物(9),在叔丁醇钾的作用下,化合物9很容易关环得到最终产物1,2-内醚糖.

The title compound was synthesized from L-rhamnose by a series of steps. The key intermediate for the synthesis was 2-O acetyl-3, 4-di-O-benzyl 6-deoxy-a-L-talopyra nosyl chloride, which was converted into the target compound by ring closure with potassium tert-butoxide. The 1H NMR spectrum of the anhydro sugar was determined by the use of single frequency decoupling. The new compounds obtained in the synthesis were identified by their 1H NMR spectra,elemental analysis,mass spectra and optical rotation.