120312-08-5Relevant academic research and scientific papers
Toward the solid-phase synthesis of heparan sulfate oligosaccharides: Evaluation of iduronic acid and idose building blocks
Guedes, Nerea,Czechura, Pawel,Echeverria, Begona,Ruiz, Ada,Michelena, Olatz,Martin-Lomas, Manuel,Reichardt, Niels-Christian
, p. 6911 - 6934 (2013/08/23)
Glycan arrays have been established as the premier technical platform for assessing the specificity of carbohydrate binding proteins, an important step in functional glycomics research. Access to large libraries of well-characterized oligosaccharides rema
Modular synthesis of heparin oligosaccharides
Orgueira, Hernan A.,Bartolozzi, Alessandra,Schell, Peter,Litjens, Remy E. J. N.,Palmacci, Emma R.,Seeberger, Peter H.
, p. 140 - 169 (2007/10/03)
A general, modular strategy for the first completely stereoselective synthesis of defined heparin oligosaccharides is described. Six monosaccharide building blocks (four differentially protected glucosamines, one glucuronic and one iduronic acid) were uti
Electrochemical Oxidation of Proline Derivatives: Total Syntheses of Bulgecinine and Bulgecin C
Barrett, Anthony G. M.,Pilipauskas, Daniel
, p. 2787 - 2800 (2007/10/02)
The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented.Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsilyl)ethyl) ester (19).The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent.Bulgecin C (1c) was prepared via a β-stereoselective glycosidation reaction using a 2-azido-2-deoxy-α-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.
Glycosyl Imidates, 41. - 6-O-Benzyl-Protected Muramic Acid as Glycosyl Acceptor. - Synthesis of the GlcNAc-β-(1->4)MurNAc Disaccharide
Termin, Andreas,Schmidt, Richard R.
, p. 789 - 796 (2007/10/02)
The α-trichloroacetimidates 1 and 2 as glucosamine donors afford with the 6-O-benzyl-protected muramic acid 6a as acceptor the β-connected disaccharides 14 and 15, respectively, in high yields.Compound 14 furnishes by cleavage of the TBDMS group, transfor
