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.
Crich
David
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
Picione
John
J
D006031:Glycosylation; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D012210:Rhamnose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013450:Sulfones / Q000737:chemistry; D013865:Thioglycosides / Q000737:chemistry
D011714:Pyrans; D013450:Sulfones; D013865:Thioglycosides; D012210:Rhamnose