Markad Shankar D, Karanjule Narayan S, Sharma Tarun, Sabharwal Sushma G, Dhavale Dilip D
Garware Research Centre, Department of Chemistry, University of Pune, Pune, 411 007, India.
Org Biomol Chem. 2006 Oct 7;4(19):3675-80. doi: 10.1039/b609000a. Epub 2006 Aug 22.
The Johnson-Claisen rearrangement of D-gluco and L-ido-derived allylic orthoesters afforded gamma,delta-unsaturated ester that on ester reduction, epoxidation, regioselective oxirane opening by sodium azide and hydrogenation led to sugar amino alcohols--immediate precursors for 1-deoxy-homonojirimycin 3a,b, and polyhydroxylated homoazepanes 4a,b. Our synthetic approach and glycosidase inhibitory activity is reported.
D-葡萄糖和L-艾杜糖衍生的烯丙基原酸酯的约翰逊-克莱森重排反应生成了γ,δ-不饱和酯，该酯经酯还原、环氧化、叠氮化钠区域选择性开环环氧乙烷反应和氢化反应后得到糖氨基醇，即1-脱氧高野尻霉素3a,b和多羟基高氮杂环庚烷4a,b的直接前体。本文报道了我们的合成方法及糖苷酶抑制活性。
