Remy E. J. N. Litjens

Thioglycosides in sequential glycosylation strategies

This tutorial review surveys the use of thioglycosides in the development of sequential glycosylation methodologies, with a focus on chemoselective, orthogonal and iterative glycosylation strategies reported since the beginning of this century. Both fundamental aspects of glycosidic bond formation and ingenious state-of-the-art methodologies are presented.

A novel approach towards the stereoselective synthesis of 2-azido-2-deoxy-β-d-mannosides

Low temperature mannosylation of glycosyl acceptors under the agency of S-(4-methoxyphenyl) benzenethiosulfinate (MPBT) and trifluoromethanesulfonic anhydride (Tf2O) with p-methoxyphenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-d-mannopyranoside, readily available from d-mannosamine hydrochloride, affords 2-azido-2-deoxy-d-mannosides with high β-selectivity in good yields.

Synthesis of an α-Gal epitope α-D-Galp-(1 →3)-β-D-Galp-(1→4)-β-D-Glcp NAc-lipid conjugate

The synthesis of a neoglycoconjugate containing the Galili epitope trisaccharide connected to a spacer‐lipid entity is described. The α‐D‐Galp‐(1→3)‐β‐D‐Galp‐(1→4)‐β‐D‐GlcpNAc trisaccharide, equipped with a 3‐aminopropyl spacer, is efficiently assembled from easily accessible building blocks in a one‐pot procedure. Global deprotection of the trisaccharide and ensuing introduction of a bis(palmitamido)‐ propanamido moiety afforded title compound 1 as depicted in Scheme 1. *Dedicated to the memory of Prof. Dr. Jacques H. van Boom, our teacher, colleague, and friend.