1301693-47-9

Upstream product

• 98-88-4 benzoyl chloride 
• 77481-63-1 phenyl-1-thio-β-D-mannopyranoside 
• 1301693-24-2 phenyl 3-O-benzoyl-1-thio-β-D-mannopyranoside 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1301693-40-2 phenyl 2-azido-2-deoxy-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside 
• 1301693-36-6 phenyl 2-azido-2-deoxy-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Rapid transformation of D-mannose into orthogonally protected D-glucosamine and D-galactosamine thioglycosides

An expedient protocol for synthesis of orthogonally protected 2-azido-2-deoxy-d-glucosamine and 2-azido-2-deoxy-d-galactosamine donors from d-mannose is described. Readily available phenyl β-d-thiomannoside is rapidly transformed into d-GlcN3 thioglycosides via a highly regioselective 3-O-acylation followed by 4,6-O-benzylidenation and azide displacement of C2-OTf, which is further converted into d-GalN3 thioglycosides through Lattrell-Dax inversion of the C4 hydroxy group and its Boc protection. The reaction sequence may be completed in 2 days and involves simple workups and minimal column chromatography.