6009-45-6Relevant academic research and scientific papers
Studies of the synthesis of 1,2-cis-(cyclic carbamates) of α-D-aldopyranosylamines
Kovacs, Jozsef,Pinter, Istvan,Toth, Gabor,Gyoergydeak, Zoltan,Koell, Peter
, p. 95 - 106 (2007/10/02)
Reaction of α-D-glucopyranosyl azide with triphenylphosphine and carbon dioxide gave 1-N,2-O-carbonyl-α-D-glucopyranosylamine (7) and its α-D-furanose analogue (1), and 1-N,3-O-carbonyl-α-D-allofuranosylamine (15) and its α-D-pyranose analogue (17).Similarly, α-D-xylopyranosyl azide gave 1-N,2-O-carbonyl-α-D-xylopyranosylamine (9) and its α-D-furanose analogue (3), and 1-N,3-O-carbonyl-α-D-ribopyranosylamine (19) and its β-D-xylopyranose analogue (21).The structures of the products and their acetylated derivatives were established by 1H and 13C NMR spectroscopy. 1-N,3-O-Carbonyl-β-D-xylopyranosylamine (21) was obtained from β-D-xylopyranosyl azide when spontaneous rearrangement of the 1,2-(cyclic carbamate) 5 into 21 occurred in water.
UNPROTECTED SUGAR PHOSPHINIMINES: A FACILE ROUTE TO CYCLIC CARBAMATES OF AMINO SUGARS
Kovacs, Jozsef,Pinter, Istvan,Messmer, Andras,Toth, Gabor
, p. 57 - 66 (2007/10/02)
Unprotected sugar phosphinimines were prepared from various azido sugars by reaction with triphenylphosphine and were converted by carbon dioxide into cyclic carbamates of amino sugars.The reaction could be carried out more conveniently in a one-pot process without isolation of the phosphinimines.The 13C- and 31P-n.m.r. data for N-(β-D-glucopyranosyl)triphenylphosphine imide (2) revealed an unexpected conformation of the phosphinimine moiety (proposed as a "reverse exo-anomeric effect") stabilised by an interaction with HO-2.
