Synthesis of a unique trisaccharide having an acetal linkage between open-chain and cyclic sugar found in the cell wall of Proteus

A potential glucuronate glycosyl donor with 2-O-acyl-6,3-lactone structure: efficient synthesis of glycosaminoglycan disaccharides

“…To investigate the efficiency of our strategy, we prepared 1, O-benzyl protected glucuronolactone derivative 2 8 , and a corresponding set of standard methyl glucuronate derivatives 3 13 and 4 14 as disarmed and armed counterparts with 4 C 1 conformation, respectively. As acceptors, hexosamine derivatives 5 15 , 6 16 and 7 17 were prepared to afford chondroitin sulfate (CS), hyaluronic acid (HA), and heparan sulfate (HS) type dissaccharide units in GAGs, respectively. (Fig.…”

Expedient synthesis of a pentasaccharide related to the O-specific polysaccharide of Escherichia coli O117:K98:H4 strain

“…p-Methoxyphenyl-2-azido-4,6-O-benzylidene-2-deoxy-a-D-galactopyranoside ( 7) 21 (prepared from D-galactal) was treated with sodium cyanoborohydride 22 in the presence of HCl in Et 2 O to give 3,4-dihydroxy derivative, which on treatment with triethyl orthoacetate in the presence of p-toluenesulfonic acid, 23 followed by acid hydrolysis of the orthoester, furnished 26,27 in acetonitrile furnished a trisaccharide diol derivative, which was selectively benzoylated at the primary hydroxyl group using benzoyl cyanide 28 and pyridine to give trisaccharide acceptor 12 in 76% yield in two steps (Scheme 1).…”

Chemical synthesis and immunological evaluation of entirely carbohydrate conjugate Globo H-PS A1

“…Therefore, our synthesis commenced with preparing trisaccharide donor 5 using monosaccharide intermediates 7, 74 8, 75 and 9 71,76 (Scheme 1). They were assembled in a linear sequence given rise to trisaccharide 13 (Scheme 2).…”