697298-48-9Relevant academic research and scientific papers
Synthesis and kinetic evaluation of 4-deoxy-4-phosphonomethyl-D- erythronate, the first hydrolytically stable and potent competitive inhibitor of ribose-5-phosphate isomerase
Burgos, Emmanuel,Salmon, Laurent
, p. 3465 - 3469 (2004)
4-deoxy-4-Phosphonomethyl-D-erythronate, an isosteric and hydrolytically stable analogue of the known ribose-5-phosphate isomerase inhibitor 4-deoxy-4-phospho-D-erythronate, was obtained by a 14-step synthesis from D-arabinose through an highly improved s
Side Chain Conformation and Its Influence on Glycosylation Selectivity in Hexo- and Higher Carbon Furanosides
Siyabalapitiya Arachchige, Sameera,Crich, David
, p. 316 - 339 (2021/12/27)
We describe the synthesis and side chain conformational analysis of a series of four 6-deoxy-2,3,5-tri-O-benzyl hexofuranosyl donors with the d-gluco, l-ido, d-altro, and l-galacto configurations. The conformation of the exocyclic bond of these compounds depends on the relative configuration of the point of attachment of the side chain to the ring and of the two flanking centers and can be predicted on that basis analogously to the heptopyranose analogs. Variable-temperature nuclear magnetic resonance (VT NMR) spectroscopy of the activated donors reveals complex, configuration-dependent mixtures of intermediates that we interpret in terms of fused and bridged oxonium ions arising from participation by the various benzyl ethers. The increased importance of ether participation in the furanoside series compared to the pyranosides is discussed in terms of the reduced stabilization afforded to furanosyl oxocarbenium ions by covalent triflate formation. The stereoselectivities of the four donors are discussed on the basis of the benzyl ether participation model.
Synthesis of C-disaccharide analogues of the α-D-arabinofuranosyl- (1→5)-α-D-arabinofuranosyl motif of mycobacterial cell walls via alkynyl intermediates
Aslam, Tashfeen,Fuchs, Michael G. G.,Le Formal, Adeline,Wightman, Richard H.
, p. 3249 - 3252 (2007/10/03)
Two C-glycosides related to the recurrent α-D-arabinofuranosyl- (1→5)-α-D-arabinofuranosyl structural motif of mycobacterial arabinan have been prepared by routes involving acetylenic intermediates.
Enantiospecific synthesis of the phospholipase A2 inhibitor (-)-cinatrin B
Cuzzupe, Anthony N.,Di Florio, Romina,Rizzacasa, Mark A.
, p. 4392 - 4398 (2007/10/03)
The first enantiospecific synthesis of phospholipase A2 (PLA2) inhibitor (-)-cinatrin B (2) from the D-arabinose derivative 9 is described. The spirolactone system was formed by an Ireland-Claisen rearrangement of the allyl ester 8 followed by hydrolysis and stereoselective iodolactonization. The stereoselectivity of the rearrangement was controlled by the asymmetry in the allylic alcohol fragment. Ester (S)-8 gave the desired rearrangement product 7 and the epimer 13 in high yield as a 73:27 ratio, respectively. The final stereocenter at C2 was introduced via a chelation-controlled addition of the Grignard reagent derived from trimethylsilylacetylene to α-hydroxy ketone 6. Transformation of the terminal alkyne into the methyl ester 21 followed by acetal hydrolysis and selective lactol oxidation afforded cinatrin B methyl ester (22). Base hydrolysis and acid-induced relactonization then gave (-)-cinatrin B (2).
Stereoselective synthesis of 5-methylphosphono-D-arabino hydroximolactone, inhibitor of glucosamine-6-phosphate synthase and phosphoglucose isomerase
Le Camus, Corentin,Chassagne, Alexia,Badet-Denisot, Marie-Ange,Badet, Bernard
, p. 287 - 288 (2007/10/03)
Compound 2, synthesized from D-arabinose in 12 steps with an overall 4% yield, is a competitive inhibitor vs fructose-6P for both phosphoglucose isomerase and glucosamine-6P synthase.
