96016-77-2

Upstream product

• 96022-39-8 methyl 4-azido-2,3-di-O-benzyl-4-deoxy-α-L-arabinopyranoside 
• 100-39-0 benzyl bromide 
• 18390-72-2 methyl 4-azido-4-deoxy-β-L-arabinopyranoside 
• 1259066-53-9 allyl 4-azido-4-deoxy-β-L-arabinopyranoside 

Relevant academic research and scientific papers

Stereoselective synthesis of α- and β-L-Ara4N glycosyl H-phosphonates and a neoglycoconjugate comprising glycosyl phosphodiester linked β-L-Ara4N

Stereoselective synthesis of variably protected α- and β-L-Ara4N glycosyl H-phosphonates as key intermediates in the syntheses of β-L-Ara4N-modified LPS structures and α-L-Ara4N-containing biosynthetic precursors is reported. A facile one-pot approach toward β-L-Ara4N glycosyl H-phosphonates includes anomeric deallylation of protected 4-azido β-L-Ara4N via terminal olefin isomerization followed by ozonolysis and methanolysis of formyl groups to furnish exclusively β-configured lactols that are phosphitylated with retention of configuration. The carbohydrate epitope of β-L-Ara4N-modified Lipid A, βGlcN(1→6)αGlcN(1→P←1)β-L-Ara4N, was stereoselectively synthesized and linked to maleimide-activated bovine serum albumin.

Synthesis of C-glycosyl phosphonate derivatives of 4-amino-4-deoxy-α-L-arabinose

The incorporation of basic substituents into the structurally conserved domains of cell wall lipopolysaccharides has been identified as a major mechanism contributing to antimicrobial resistance of Gram-negative pathogenic bacteria. Inhibition of the corr

Synthesis of neoglycoconjugates containing 4-amino-4-deoxy- l -arabinose epitopes corresponding to the inner core of burkholderia and proteus lipopolysaccharides

Disaccharides that contain 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo) and D-glycero-D-talo-oct-2-ulosonic acid (Ko) substituted at the 8-position by 4-amino-4-deoxy-β-L-arabinopyranosyl (Ara4N) residues have been prepared. Coupling an N-phenyltrifluoroacetimidate-4-azido-4-deoxy-L-arabinosylglycosyl donor to acetyl-protected allyl glycosides of Kdo and Ko afforded anomeric mixtures of disaccharide products in 74 and 90 % yield, respectively, which were separated by chromatography. Further extension of an intermediate Ara4N-(1→8)-Kdo disaccharide acceptor, which capitalized on a regioselective glycosylation with a Kdo bromide donor under Helferich conditions, afforded the branched trisaccharide α-Kdo-(2→4)[β-L- Ara4N-(1→8)]-α-Kdo derivative. Deprotection of the protected di- and trisaccharide allyl glycosides was accomplished by TiCl4-promoted benzyl ether cleavage followed by the removal of ester groups and reduction of the azido group with thiol or Staudinger reagents, respectively. The reaction of the anomeric allyl group with 1,3-propanedithiol under radical conditions afforded the thioether-bridged spacer glycosides, which were efficiently coupled to maleimide-activated bovine serum albumin. The neoglycoconjugates serve as immunoreagents with specificity for inner core epitopes of Burkholderia and Proteus lipopolysaccharides.