1382230-41-2

Upstream product

• 181136-65-2 phenyl 2,3,4-tri-O-acetyl-1-thio-6-deoxy-β-L-mannopyranoside 
• 503065-75-6 phenyl 1-thio-6-deoxy-β-L-mannopyranoside 
• 5158-64-5 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide 
• 1382229-08-4 phenyl 2-O-sulfonylbenzyl-4-O-TIPS-1-thio-β-L-rhamnopyranoside 
• 108-93-0 cyclohexanol 
• 1382229-04-0 C₁₉H₂₂O₆S₂ 
• 1382228-97-8 phenyl 3,4-di-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-L-rhamnopyranoside 

Relevant academic research and scientific papers

Rhamnosylation: Diastereoselectivity of conformationally armed donors

The α/β-selectivity of super-armed rhamnosyl donors have been investigated in glycosylation reactions. The solvent was found to have a minor influence, whereas temperature was crucial for the diastereoselectivity. At very low temperature, a modest β-selectivity could be obtained, and increasing temperature gave excellent α-selectivity. The donors were highly reactive, and activation was observed at temperatures as low as -107 °C. Different promoter systems and leaving groups were investigated, and only activation with a heterogeneous catalyst increased the amount of the β-anomer significantly. By introducing an electron-withdrawing nonparticipating group, benzyl sulfonyl, on 2-O, an increase in β-product was observed.