131614-82-9Relevant academic research and scientific papers
Enantiomeric 2-acetamido-1,4-dideoxy-1,4-iminoribitols as potential pyrrolidine hexosaminidase inhibitors
Rountree, J.S. Shane,Butters, Terry D.,Dwek, Raymond A.,Fleet, George W.J.
scheme or table, p. 126 - 133 (2012/02/02)
2-Acetamido-1,4-imino-1,2,4-trideoxy-D-ribitol (DRBNAc) and the enantiomeric LRBNAc were prepared as potential hexosaminidase inhibitors from L- and D-lyxonolactone, respectively. Neither N-benzyl-DRBNAc nor N-benzyl-LRBNAc showed any inhibition of α- or
Efficient synthesis from d-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-l-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases
Rountree, J.S.Shane,Butters, Terry D.,Wormald, Mark R.,Dwek, Raymond A.,Asano, Naoki,Ikeda, Kyoko,Evinson, Emma L.,Nash, Robert J.,Fleet, George W.J.
, p. 4287 - 4291 (2008/02/12)
The synthesis from d-lyxonolactone of 2-acetamido-1,4-imino-1,2,4-trideoxy-l-arabinitol LABNAc proceeded in an overall yield of 25%; the enantiomer, 2-acetamido-1,4-imino-1,2,4-trideoxy-d-arabinitol DABNAc, was prepared from l-lyxonolactone. LABNAc and N-
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 from D-lyxonolactone of 1,4-dideoxy-1,4-imino-L-arabinitol, a glucosidase inhibitor with in vitro anti-viral activity
Behling, James R.,Campbell, Arthur L.,Babiak, Kevin A.,Ng, John S.,Medic, John,Farid, Payman,Fleet, George W. J.
, p. 3359 - 3366 (2007/10/02)
Benzylidenation is the only protection required in a 7 step synthesis of the hydrochloride of 1,4-dideoxy-1,4-imino-L-arabinitol from D-lxyonolactone in an overall yield of 21%.
Use of D-Ribonolactone in Organic Synthesis. 2. Scope and Utility
Chen, Shin-Yih,Joullie, Madeleine M.
, p. 2168 - 2174 (2007/10/02)
The scope and utility of D-ribonolactone (1) as chiral template for the synthesis of optically active γ-lactones which are important precursors for many natural products are discussed.The regio- and stereoselective functionalization of 1 is examined.
