503066-02-2

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 2774-19-8 (2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 503065-97-2 phenyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-1-thio-β-L-rhamnopyranoside 

Relevant academic research and scientific papers

On the nitrile effect in l-rhamnopyranosylation

It is shown that the use of 5% acetonitrile or propionitrile in dichloromethane functions to increase the β-selectivity of a number of l-rhamnopyranosylation reactions conducted by the thioglycoside method with activation by the 1-benzenesulfinyl piperidi

Direct synthesis of the beta-l-rhamnopyranosides.

The direct formation of beta-l-rhamnopyranosides by means of thioglycoside donors protected with a 2-O-sulfonate ester and, ideally, a 4-O-benzoyl ester, is reported. Activation is achieved with the combination of 1-benzenesulfinyl piperidine and triflic anhydride in the presence of 2,4,6-tri-tert-butylpyrimidine. Selectivities vary from moderate to good, and the sulfonyl group is easily removed post-glycosylation with sodium amalgam in 2-propanol.