Preparation of a glycosyl donor suitable for synthesis of glycoprotein "core" oligosaccharides.
2-O-Acetyl-3-O-allyl-4-O-benzyl-6-O-tert-butyldiphenylsilyl-D-gluc opyranosyl 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)-alpha-D-glucopyranos e. Silver triflate-promoted coupling of 14 with benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside gave a protected beta-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.
D005960:Glucosides / Q000138:chemical synthesis*; D006023:Glycoproteins / Q000138:chemical synthesis; D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009844:Oligosaccharides / Q000138:chemical synthesis*
D005960:Glucosides; D006023:Glycoproteins; D006027:Glycosides; D007202:Indicators and Reagents; D009844:Oligosaccharides; C045836:2-O-acetyl-3-O-allyl-4-O-benzyl-6-O-tert-butyldiphenylsilylglucopyranosyl chloride