Oligomeric Thioglycosides with α-<SCP>d</SCP>-manno-(1‘→2) Linkages from a Glycal-1,2-episulfide

<UFIGR ID="ol990702xn00001">Under basic conditions, phenyl 1,2-dithio-α-<SCP>d</SCP>-mannopyranoside forms a glycal-1,2-episulfide, which undergoes controlled oligomerization to afford a family of thio-oligo-α-<SCP>d</SCP>-mannopyranosides in a single reaction. The episulfide can also be intercepted by added thiolates, which leads to other sorts of thioglycosides. These α-(1→2)-linked thio-mannopyranosides might have application as mimics of natural structures such as viral high-mannose glycoproteins or ManLAM.