6<i>R</i>/<i>S</i>-deutero-α-<span style="font-variant: small-caps">d</span>-mannopyranoside 1-phosphate

Abstract

6R/S-deutero-α-d-mannopyranoside 1-phosphate was synthesised from a C6 aldehydic mannose thioglycoside donor in four steps. Using NaBD4 as the reductant, isotopic enrichment at C6 was achieved and the resultant C6-deuterated material was converted through to the glycosyl 1-phosphate using a protection/glycosylation/deprotection sequence. The product was fully characterised by 1H, 13C, 31P and 2D NMR, alongside MS analysis.

Keywords

• mannose
• glycosyl-phosphate
• deuterium
• isotope
• NMR