1382229-72-2

Upstream product

• 1214-98-8 phenyl 1-thio-α-L-rhamnopyranose 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 109-86-4 2-methoxy-ethanol 
• 1382228-82-1 phenyl 2-O-benzyl-3,4-di-O-TIPS-1-thio-α-L-rhamnopyranoside 
• 849938-16-5 phenyl 2-O-benzyl-1-thio-α-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.