56543-11-4Relevant academic research and scientific papers
A heterogeneous Pd-Bi/C catalyst in the synthesis of l-lyxose and l-ribose from naturally occurring d-sugars
Fan, Ao,Jaenicke, Stephan,Chuah, Gaik-Khuan
supporting information; experimental part, p. 7720 - 7726 (2011/12/04)
A critical step in the synthesis of the rare sugars, l-lyxose and l-ribose, from the corresponding d-sugars is the oxidation to the lactone. Instead of conventional oxidizing agents like bromine or pyridinium dichromate, it was found that a heterogeneous catalyst, Pd-Bi/C, could be used for the direct oxidation with molecular oxygen. The composition of the catalyst was optimized and the best results were obtained with 5:1 atomic ratio of Pd:Bi. The overall yields of the five-step procedure to l-ribose and l-lyxose were 47% and 50%, respectively. The synthetic procedure is advantageous from the viewpoint of overall yield, reduced number of steps, and mild reaction conditions. Furthermore, the heterogeneous oxidation catalyst can be easily separated from the reaction mixture and reused with no loss of activity.
Looking glass inhibitors: Efficient synthesis and biological evaluation of D-deoxyfuconojirimycin
Bleriot, Yves,Gretzke, Dirk,Kruelle, Thomas M.,Butters, Terry D.,Dwek, Raymond A.,Nash, Robert J.,Asano, Naoki,Fleet, George W.J.
, p. 2713 - 2718 (2007/10/03)
1,6-Dideoxygalactostatin, the mirror image of 1-deoxy-L-fuconojirimycin, was efficiently prepared from 2,3-O-isopropylidene-L-lyxonolactone in four steps and evaluated as a glycosidase inhibitor.
Spectroscopic, crystallographic and computational studies of the formation and isomerization of cyclic acetals and ketals of pentonolactones
Han,Joullie,Fokin,Petasis
, p. 2535 - 2562 (2007/10/02)
The different reactivities of D-ribonolactone, L-arabinonolactone, D-xylonolactone, D-lyxonolactone and 2-deoxy-D-ribonolactone toward benzaldehyde and acetone in acidic media, were examined. The reactions involved complex equilibria and were investigated with extensive 13C NMR studies as well as X-ray crystallographic analysis of selected products. Molecular mechanics (MM2) and semiempirical (PM3 and AM1) calculations of some derivatives were carried out in order to facilitate structural and conformational assignments. The differences in reactivity observed for the reactions of D-pentono-1,4-lactones with benzaldehyde and acetone are rationalized in terms of their structural and conformational features.
Synthesis of L-Ribono- and L-Lyxono-lactone
Kold, Henriette,Lundt, Inge,Pedersen, Christian
, p. 675 - 678 (2007/10/02)
L-Ribonolactone has been prepared in good yield by treatment of 2,3-O-isopropylidene-5-O-methanesulfonyl-D-lyxono-1,4-lactone with aqueous base.It was isolated as 3,4-O-benzylidene-L-ribono-1,5-lactone.A similar treatment of 2,3-O-isopropylidene-5-O-methanesulfonyl-D-ribono-1,4-lactone gave L-lyxonolactone, isolated as the 3,5-O-benzylidene derivative.The mechanisms of the reactions, as well as those of the reaction of 5-bromo-5-deoxy-D-ribono- and -D-lyxono-1,4-lactone, with aqueous base have been studied.
Short efficient synthesis of the α-L-fucosidase inhibitor, deoxyfuconojirimycin [1,5-dideoxy-1,5-imino-l-fucitol] from d-lyxonolactone
Fleet, George W. J.,Petursson, Sigthor,Campbell, Arthur L.,Mueller, Richard A.,Behling, James R.,Babiak, Kevin A.,Ng, John S.,Scaros, Mike G.
, p. 665 - 666 (2007/10/02)
The only protection required in a five-step synthesis of the α-L-fucosidase inhibitor, deoxyfuconojirimycin [1,5-dideoxy-1,5-imino-L- fucitol] from D-lyxonolactone, a readily available chiral pool material, is a single isopropylidene group.
