259544-09-7

Upstream product

• 155301-04-5 octyl 4,6-di-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-gulopyranoside 
• 917-54-4 methyllithium 
• 259544-08-6 octyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-4,6-di-O-benzyl-β-D-xylo-hexopyranosid-3-ulose 

Relevant academic research and scientific papers

A novel and efficient synthesis of a highly active analogue of clasto-lactacystin β-lactone

Herein, we describe a new convergent synthesis of a more potent analogue of clasto-lactacystin β-lactone (2), PS-519 compound 4, which is currently in preclinical development for the treatment of ischemia-reperfusion injury in stroke and myocardial infarction. The synthetic strategy relies on building two intermediates (an oxazoline and an aldehyde) which are joined through a doubly diastereoselective aldol reaction, setting up the requisite unichiral centers in the final product (4). The facial selectivity and ultimate stereocontrol are achieved by employing a trivalent aluminum Lewis acid, Me2AlCl, in a chelation-induced reaction which yields a single aldol adduct. The efficiency of the synthetic approach has allowed for the preparation of multigram quantities of clinical grade material, which will support Phase I studies.

Chemoenzymatic synthesis of α-(1→3)-Gal(NAc)-terminating glycosides of complex tertiary sugar alcohols

The scope of glycosyltransferases in the synthesis of oligosaccharide analogues has been expanded to include the use of "retaining" enzymes acting on complex tertiary C-branched disaccharide acceptors. The enzymes studied were α1,3-galactosyltransferase (