The use of tri-O-acetyl-D-glucal and -D-galactal in the synthesis of 3-acetamido-2,3-dideoxyhexopyranoses and -hexopyranosides.
Addition of hydrazoic acid to alpha,beta-unsaturated aldehydes derived from tri-O-acetyl-D-glucal and -D-galactal gave 3-azido-2,3-dideoxyhexopyranoses. These were converted into 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxyhexopyranoses as well as methyl and ethyl glycosides. Hydrogenation of the proamine group in 3-azido-2,3-dideoxy derivatives provided different 3-amino and 3-acetamido sugars. The configuration and conformation of all products were established on the basis of the 1H and 13 C NMR, IR and polarimetric data.
Liberek
Beata
B
Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, PL-80-952 Gdańsk, Poland.
Dabrowska
Aleksandra
A
Frankowski
Ryszard
R
Matuszewska
Marlena
M
Smiatacz
Zygfryd
Z
D000117:Acetylglucosamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D003837:Deoxy Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000737:chemistry*; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry*; D006601:Hexoses / Q000138:chemical synthesis* / Q000737:chemistry; D009904:Optical Rotation
C474960:3-acetamido-2,3-dideoxyhexopyranose; D003837:Deoxy Sugars; D006601:Hexoses; C001289:d-glucal; C002038:galactal; D003847:Deoxyglucose; D000117:Acetylglucosamine; D005690:Galactose