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Upstream product

• 457931-46-3 4-methylphenyl 1-thio-α-D-mannopyranoside 
• 942043-27-8 4-methylphenyl 2,3,4,6-tetra-O-trimethylsilyl-1-thio-α-D-mannopyranoside 
• 1157902-57-2 4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

Regioselective and stereoselective benzylidene installation and one-pot protection of d-mannose

Oligosaccharide syntheses are an important source of well-defined sugar constructs particularly needed for the evaluation of structure-activity relationships. The chemical assembly of oligosaccharides requires several building blocks, that is, glycosyl donors and acceptors, which are prepared in multistep processes and in a generally tedious and time-consuming manner. Having developed one-pot procedures meant to minimise the effort in sugar building block preparation, we tackled herein the one-pot preparation of fully protected and 2-, 3-, 4-, and 6-alcohol derivatives of d-mannose, a widely distributed monosaccharide. As a consequence of the hydroxyl group pattern of d-mannose, regioselective and stereoselective benzylidenations were developed and later seamlessly utilised as the first transformation in the one-pot procedure.