Abstract
2- O-Acetyl-3- O-allyl-4- O-benzyl-6- O-tert-butyldiphenylsilyl- d-glucopyranosyl chloride ( 14), a glycosyl donor suitable for synthesis of oligosaccharides corresponding to the N-glycoprotein saccharide “core”, was synthesized by an efficient, six-stage route from 3,4,6-tri- O-acetyl-1,2- O-[1-( exo-ethoxy)ethylidene]-α- d-glucopyranose. Silver triflate-promoted coupling of 14 with benzyl 2-acetamido-3,6-di- O-benzyl-2-deoxy-α- d-glucopyranoside gave a protected β- d-(1→4)-linked disaccharide in 38% yield, but a major side-reaction also occurred. When the tert-butyldiphenylsilyl group was quantitatively removed from 14 prior to the coupling reaction, and replaced afterwards, the yield in the glycosidation was increased to 55%, and major side-products were avoided.
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.
