LiBF4-mediated C-glycosylation of glycals with allyltrimethylsilane: a facile synthesis of allyl C-glycosylic compounds.
The treatment of glycals with allyltrimethylsilane in the presence of lithium tetrafluoroborate in acetonitrile gave the corresponding allyl 2,3-unsaturated C-glycosylic compounds in excellent yields with high anomeric selectivity.
Yadav
J S
JS
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad. yadav@iict.ap.nic.in
Reddy
B V
BV
Chandraiah
L
L
Reddy
K S
KS
D001881:Borates / Q000737:chemistry*; D003847:Deoxyglucose / Q000031:analogs & derivatives / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D006031:Glycosylation; D007536:Isomerism; D019906:Nuclear Magnetic Resonance, Biomolecular; D013055:Spectrophotometry, Infrared; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D001881:Borates; D006027:Glycosides; D014297:Trimethylsilyl Compounds; C440777:lithium tetrafluoroborate; C043334:3,4,6-tri-O-acetylglucal; C440774:allyltrimethylsilane; D003847:Deoxyglucose