Simultaneous regioselective protection of phenyl 1-thioglucosides at the C-3 and C-6 or at the C-2 and C-6 hydroxy groups.
Simultaneous regioselective 3,6- or 2,6-selective protection of 1-thio-beta- or alpha-D-glucopyranosides is described. The C-3 and C-6 hydroxy groups of the beta-thioglucoside were selectively protected with triisopropylsilyl or tert-butyldiphenylsilyl trifluoromethanesulfonate. The C-2 and C-6 hydroxy groups of the alpha-thioglucoside were selectively protected with tert-butyldiphenylsilyl trifluoromethanesulfonate.
School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan.
Yasunori
Y
Ikeda
Ken
K
Furukawa
Hidetoshi
H
Yamada
D001593:Benzyl Compounds / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D012821:Silanes / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013379:Substrate Specificity; D013402:Sugar Alcohols / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry*
D001593:Benzyl Compounds; D012821:Silanes; D013402:Sugar Alcohols; D013865:Thioglycosides