Synthesis of the Glc3Man N-glycan tetrasaccharide by iterative allyl IAD.
The synthesis of the tetrasaccharide alpha-D-Glcp-(1-->2)-alpha-D-Glcp-(1-->3)-alpha-D-Glcp-(1-->3)-alpha-D-Manp-OMe, corresponding to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved with complete stereocontrol by the use of iterative allyl protecting group mediated intramolecular aglycon delivery (allyl IAD) demonstrating the utility of intramolecular glycosylation for the stereocontrolled construction of multiple glycosidic linkages during the synthesis of an oligosaccharide.
Attolino
Emanuele
E
Chemistry Research Laboratory, Oxford University, Mansfield Road, Oxford OX1 3TA, UK.
Cumpstey
Ian
I
Fairbanks
Antony J
AJ
D000498:Allyl Compounds / Q000737:chemistry; D006031:Glycosylation; D009844:Oligosaccharides / Q000138:chemical synthesis*
D000498:Allyl Compounds; D009844:Oligosaccharides; C512760:methyl glucopyranosyl-1-2-glycopyranosyl-1-3-glucopyranosyl-1-3-mannopyranoside