402758-84-3

Upstream product

• 23397-65-1 Methyl 2,3:5,6-di-O-benzylidene-α-D-mannofuranoside 
• 164454-52-8 methyl 3,5-O-(tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranoside 
• 100-39-0 benzyl bromide 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 402758-82-1 methyl 2-O-benzyl-α-D-arabinofuranoside 

Downstream Products

• 402758-94-5 methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-D-arabinofuranoside 
• 402758-95-6 methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(3,5-di-O-benzyl-2-O-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-α-D-arabinofuranosyl)-α-D-arabinofuranoside 
• 402758-93-4 methyl 2-O-benzyl-5-O-t-butyldiphenylsilyl-3-O-(2-O-benzoyl-3,5-di-O-benzyl-α-D-arabinofuranosyl)-α-arabinofuranoside 

Relevant academic research and scientific papers

Total synthesis of (+)-epiquinamide and (?)-epiepiquinamide from D-mannose

The total synthesis of (+)-epiquinamide and (?)-epiepiquinamide has been achieved starting from a 3,5-dihydroxyfuranoside synthon derived from D-mannose. The methods featured Bernet-Vasella reaction followed by Horner-Wadsworth-Emmons (HWE) reaction to provide a new chiral building block diene as the key steps. The bicyclic framework of this quinolizidine was constructed by using ring-closing metathesis, selective reduction of ester and intramolecular nucleophilic substitution-cyclization.

Arabinofuranosides from mycobacteria: Synthesis of a highly branched hexasaccharide and related fragments containing β-arabinofuranosyl residues

The synthesis of 11 oligosaccharides (4-14) containing β-arabinofuranosyl residues is reported. The glycans are all fragments of two polysaccharides, arabinogalactan and lipoarabinomannan, which are found in the cell wall complex of mycobacteria. In the preparation of the targets, the key step was a low-]temperature glycosylation reaction that installed the β-arabinofuranosyl residues with good to excellent stereocontrol.