Synthesis of an Unnatural N-Glycan-linked Dolichyl Pyrophosphate Precursor

Abstract

  An unnatural α-D-mannopyranose-linked chitobiosyl dolichyl pyrophosphate, a stereoisomer of the N-glycan biosynthesis intermediate, was synthesized. The protected trisaccharide, α-D-Man-(1→4)-β-D-GlcNAc-(1→4)-D-GlcNAc, carrying a 4-methylbenzoyl group was prepared for the convenience of a TLC analysis. 1-O-Phosphorylation, condensation with dolichyl phosphate, and subsequent deprotection afforded the title compound.