首页 | 本学科首页   官方微博 | 高级检索  
     检索      


Glycosylated vinyl ethers by the Julia–Lythgoe–Kocienski olefination: application to the synthesis of 2′,5′-dideoxydisaccharides and carbohydrated β-lactams
Authors:Ivn Prez Snchez  Edward Turos
Institution:aCenter for Molecular Diversity in Drug Design, Discovery, and Delivery, Department of Chemistry, University of South Florida CHE 205, 4202 East Fowler Avenue, Tampa, FL 33620, USA
Abstract:α-Carbohydrated pyridinyl sulfones, prepared from commercially available d-(−)-ribose, d-(+)-galactose, and d-(+)-glucose through a five-step sequence, have been employed in the Julia–Lythgoe–Kocienski olefination with aldehydes. This one-pot protocol, using solid KOH at room temperature, affords the corresponding glycosidic enol ethers in moderate to excellent yields and (E)-stereoselectivities. These glycosylated adducts undergo hetero-Diels–Alder reactions with 2-formyl-1-malondialdehyde to afford 2′,5′-dideoxygenated disaccharides in good yields and complete regio- and endo-selectivity. Alternatively, the 2+2]-cycloaddition reaction of the glycosidic enol ethers with chlorosulfonyl isocyanate provided glycosylated β-lactams regioselectively and with only trans-stereoselectivity. The β-lactams could be converted to N-methylthio derivatives which show decent antibacterial activity toward methicillin-resistant strains of Staphylococcus aureus.
Keywords:
本文献已被 ScienceDirect 等数据库收录!
设为首页 | 免责声明 | 关于勤云 | 加入收藏

Copyright©北京勤云科技发展有限公司  京ICP备09084417号