Efficient Synthesis of a Stereochemically Defined Carbohydrate Scaffold:  Carboxymethyl 2-Acetamido-6-Azido- 4-O-Benzyl-2-deoxy-α-d-Glucopyranoside

Regioselective reductive openings of 4,6-benzylidene acetals: synthetic and mechanistic aspects

“…Interestingly, when Ghosh et al repeated the reaction using a different substrate, the regioselectivity was the opposite and 6-O-benzyl ether was isolated in 60% yield. 41 So far, the best results for formation of the 6-O-benzyl ether (43) from compound 21 (95% yield) is the use of NaCNBH 3 in combination with I 2 in MeCN. 21 This method was developed for the same reason as above, to find a reagent combination that was easier to handle (comparing to moisture sensitive triflates or HCl).…”

High-throughput Chemistry toward Complex Carbohydrates and Carbohydrate-like Compounds a

“…scaffold based on 2-acetamido-2-deoxy-D-glucose containing an azide group at C-6, a hydroxyl group at C-4 and a carboxylic acid functionality at C-1 [38]. The authors allude to a 12000 compound library, but no details are given.…”

Orthogonally Protected Sugar Diamino Acids as Building Blocks for Linear and Branched Oligosaccharide Mimetics

“…Sugar amino acids (SAAs), [1] which are carbohydrate derivatives with both an amino group and a carboxyl group connected to the carbohydrate frame, have found wide application as building blocks for oligosaccharide [2,3] and peptide mimetics, [4,5] as secondary-structure inducing elements, and as pharmacophore-presenting scaffolds [6] for the generation of combinatorial libraries. [7] Used as monomers with a rigid pyran ring, functional pharmacophoric groups attached to the hydroxy, amino, and carboxyl groups can be presented in a distinct spatial arrangement as was demonstrated in seminal studies by Hirschmann et al [8] Linear and cyclic oligomers of SAAs have been synthesized, taking advantage of well-established peptide chemistry, and in certain cases they adopt defined secondary structures.…”