K. Toshima et al., IMPROVED PRACTICAL METHOD FOR SYNTHESIS OF ARYL C-GLYCOSIDES FROM UNPROTECTED METHYL GLYCOSIDES AND 1-HYDROXY SUGARS, Journal of the Chemical Society, Chemical Communications, (8), 1994, pp. 997-998
Aryl C-glycosidations of the unprotected methyl glycosides 9-12 and th
e unprotected 1-hydroxy sugars 14 and 15 with 2-naphthol 6 using TMSOT
f proceed much more effectively than those of the acylated methyl glyc
osides 4 and 5; the unprotected methyl glycoside 10 is also smoothly c
oupled with other phenol and naphthol derivatives 25-27 to give the co
rresponding unprotected o-hydroxyaryl beta-C-glycosides in high yields
(TMSOTf = trimethylsilyloxytrifluoromethanesulfonate).