84774-52-7Relevant academic research and scientific papers
α-Amino Polyhydroxy Tetronic and Pentonic Acids from Bromodeoxyaldonolactones
Bols, Mikael,Lundt, Inge
, p. 67 - 74 (2007/10/02)
Treatment of either 2-bromo-2-deoxy-L-threono-(3) or L-erythrono-1,4-lactone (6) with NaN3 gave identical mixtures of 2-azido-2-deoxy-L-threono- (7) and -L-erythronolactone (8).Similar treatment of 2-bromo-2-deoxy-D-xylono-1,4-lactone (13) gave a 1:1 mixture of 2-azido-2-deoxy-D-xylono- (15) and -D-lyxono-1,4-lactone (16), while the 2-bromo-2-deoxy-D-arabinono-1,4-lactone (24) gave a 1:1 mixture of 2-azido-2-deoxy-D-arabinono- (26) and D-ribono-1,4-lactone (27).All isomers could be separated by either flash chromatography or crystallization.Catalytic hydrogenation of the azido lactones gave the corresponding amino lactones, as hydrochlorides, or the α-amino acids.The azido lactone 15 was converted into 2-acetamido-2-deoxy-D-xylose (21), while 26 gave 2-amino-2-deoxy-D-arabinose * HCl (35).The epimeric mixture of azido lactones (15,16) or (26,27) were converted in a one-pot synthesis into 2-acetamido-5-O-acetyl-2,3-dideoxy-D-threo-pentono-1,4-lactone (37).The intermediate was shown to be 2-acetamido-5-O-acetyl-2,3-dideoxy-D-glycero-pent-2-eno-1,4-lactone (36), which was prepared from the fully acetylated amino lactones (32,33).The bromo lactones, as well as the 2-azido lactones, were shown to equilibrate under basic conditions.
SYNTHESE DES 2-AMINO-2-DESOXY-D-ARABINONO- ET -D-XYLONO-LACTONES PAR CONDENSATION D'ACIDES AMINES AVEC LE D-GLYCERALDEHYDE. ANALYSE STRUCTURALE PAR RAYONS X DE DEUX DERIVES
Depezay, Jean-Claude,Dureault, Annie,Prange, Thierry
, p. 51 - 62 (2007/10/02)
Synthesis of 2-amino-2-deoxy-D-pentonolactones was performed by diastereoselective hydroxyalkylation of 2,3-O-isopropylidene-D-glyceraldehyde with ethyl isocyanoacetate, to give two oxazolines in a ratio of 7:3.Hydrolysis gave first the corresponding amid
