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A Catalytic and Stereoselective Glycosylation with β ‐Glycosyl Fluorides
Author(s) -
Mukaiyama Teruaki,
Takeuchi Kazuya,
Jona Hideki,
Maeshima Hisashi,
Saitoh Terunobu
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20000809)83:8<1901::aid-hlca1901>3.0.co;2-q
Subject(s) - chemistry , glycosyl , glycosylation , stereoselectivity , catalysis , fluoride , glycosyl donor , organic chemistry , solvent , glycoside , trifluoromethyl , benzene , combinatorial chemistry , inorganic chemistry , biochemistry , alkyl
A catalytic and stereoselective glycosylation of several glycosyl acceptors with β ‐ D ‐glycosyl fluoride was successfully performed in the presence of a catalytic amount of trityl tetrakis(pentafluorophenyl)borate (TrB(C 6 F 5 ) 4 ) or trifluoromethanesulfonic acid (TfOH). When TrB(C 6 F 5 ) 4 was used as a catalyst in the solvent pivalonitrile/(trifluoromethyl)benzene 1 : 5, the glycosylation proceeded smoothly to afford the glycosides in high yields with high β ‐ D ‐stereoselectivities (see Table 3 ). Further, the glycosylation by the armed‐disarmed strategy in the presence of this catalyst was established (see Table 4 ). Similarly, glycosylation catalyzed by the strong protic acid TfOH afforded the corresponding β ‐ D ‐glycosides in good‐to‐excellent yields on treating β ‐ D ‐ glycosyl fluorides having a 2‐ O ‐benzoyl group with various glycosyl acceptors including thioglycosides (see Tables 6 and 7 ).