Abstract
The synthesis of the ethoxycarbonyloctanyl glycoside of the Lewis-Y (Ley) tetrasaccharide, a part of complex glycosphingolipids, was based on the trichloroacetimidate method for glycoside synthesis. The regioselective introduction of protective groups and the high yield of epimers of the azidonitration reaction applied to O-[2,3,4-tri-O-acetyl-6-O-[dimethyl-(2,3-dimethyl-2-butyl)silyl]-beta-D- galactopyranosyl]-(1-->4)-3-O-acetyl-1,5-anhydro-6-O-[dimet hyl-(2,3- dimethyl-2-butyl)silyl]-D-arabino-hex-1-enitol led to a lactosamine acceptor molecule. The double specific introduction of an alpha-L-fucosyl group in high yield gave a protected Ley-tetrasaccharide. After activation to give the alpha-trichloroacetimidate, specific beta-glycosylation with 8-ethoxycarbonyl octanol under SN 2 condition, followed by cleavage of all protective groups led to the tetrasaccharide, alpha-L-Fucp-(1-->2)-beta-D-galp-(1-->4)-[alpha-L-fucp-(1--> 3)]-beta-D- GlcpNAcO(CH2)8CO2Et in high yield.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
