[Glycosylation of 5-Phenyl-1,3,4-oxadiazole-2-thiol with alpha-D-glucopyranosyl chloride under phase transfer conditions].
5-Phenyl-1,3,4-oxadiazole-2-thiol is glycosylated easily and in high yields with 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosyl chloride in the presence of catalytic amounts of aliphatic and aromatic crown ethers under phase transfer (solid-organic solvent) conditions. The reaction rate and the ratio of the resulting N- and S-regioisomers depend on the catalyst nature.
Kur'ianov
V O
VO
Kotliar
S A
SA
Prisoka
U S
US
Chupakhina
T A
TA
Chirva
V Ia
VIa
D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D006031:Glycosylation; D010069:Oxadiazoles / Q000737:chemistry*
C515413:3,4,6-tri-O-acetyl-2-acetamido-2-deoxyglucopyranosyl chloride; C515412:5-phenyl-1,3,4-oxadiazole-2-thiol; D010069:Oxadiazoles; D000117:Acetylglucosamine