Beta-selective O-rhamnosylation with a rhamnosyl trichloroacetimidate that has the 4C1 conformation.
A beta-selective rhamnosylation reaction was accomplished by using 2-O-benzyl-3-O-tert-butyldimethylsilyl-4-O-tertbutyldiphenylsilyl-alpha-L-rhamnopyranosyl trichloroacetimidate and a catalytic amount of 9-borabicylco[3.3.1]nonyl trifluoromethanesulfonate. The rhamnosyl donor has the 4C1 ring conformation to change the general high alpha-selectivity of the rhamnosylation reactions.
Ikeda
T
T
School of Science, Kwansei Gakuin University, Nishinomiya, Japan.
Yamada
H
H
D000081:Acetamides; D062845:Chloroacetates; D008968:Molecular Conformation; D015394:Molecular Structure; D012210:Rhamnose / Q000031:analogs & derivatives* / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013696:Temperature; D014238:Trichloroacetic Acid / Q000737:chemistry*
D000081:Acetamides; D062845:Chloroacetates; D014238:Trichloroacetic Acid; C009528:trichloroacetamide; D012210:Rhamnose