206751-88-4

Upstream product

• 3282-30-2 pivaloyl chloride 
• 13343-62-9 benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 100-51-6 benzyl alcohol 

Downstream Products

• 3554-93-6 benzyl 2-acetamido-2-deoxy-α-D-galactopyranoside 
• 592533-31-8 2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-(2,2-dimethyl-propionyloxy)-6-hydroxymethyl-tetrahydro-pyran-4-yl ester 
• 592533-33-0 2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-2-benzyloxy-6-(2,2-dimethyl-propionyloxymethyl)-5-hydroxy-tetrahydro-pyran-4-yl ester 
• 725718-35-4 2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6R)-3-acetylamino-2-benzyloxy-6-(2,2-dimethyl-propionyloxymethyl)-5-(imidazole-1-carbothioyloxy)-tetrahydro-pyran-4-yl ester 
• 911829-45-3 2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6R)-3-acetylamino-2-benzyloxy-6-(2,2-dimethyl-propionyloxymethyl)-5-ethoxysulfinyloxy-tetrahydro-pyran-4-yl ester 
• 911829-51-1 2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6R)-3-acetylamino-2-benzyloxy-6-(2,2-dimethyl-propionyloxymethyl)-5-ethoxysulfonyloxy-tetrahydro-pyran-4-yl ester 
• 725718-36-5 2,2-Dimethyl-propionic acid (2S,3R,4S,6S)-3-acetylamino-2-benzyloxy-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester 
• 725718-43-4 2,2-Dimethyl-propionic acid (2R,3R,4S,6S)-3-acetylamino-2-(bis-benzyloxy-phosphoryloxy)-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester 
• 592533-32-9 benzyl 2-acetamido-2-deoxy-4,6-di-O-pivaloyl-α-D-galactopyranoside 
• 592533-34-1 2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6S)-5-acetylamino-6-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-4-methylsulfanylmethoxy-tetrahydro-pyran-3-yl ester 
• 592533-36-3 2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-(2,2-dimethyl-propionyloxy)-6-methylsulfanylmethoxymethyl-tetrahydro-pyran-4-yl ester 
• 592533-35-2 2,2-Dimethyl-propionic acid (2S,3R,4R,5R,6R)-3-acetylamino-2-benzyloxy-6-(2,2-dimethyl-propionyloxymethyl)-5-methylsulfanylmethoxy-tetrahydro-pyran-4-yl ester 
• 592533-41-0 2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-3-acetylamino-2-(bis-benzyloxy-phosphoryloxy)-6-(2,2-dimethyl-propionyloxymethyl)-5-methoxy-tetrahydro-pyran-4-yl ester 
• 592533-40-9 2,2-Dimethyl-propionic acid (2R,3R,4R,5R,6R)-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-2-(2,2-dimethyl-propionyloxymethyl)-4-methoxy-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Synthesis and biological evaluation of new UDP-GalNAc analogues for the study of polypeptide-α-GalNAc-transferases

A series of three O-methylated UDP-GalNAc analogues have been synthesised using a divergent strategy from a 3,6-di-O-pivaloyl GlcNAc derivative. The biological activity of these probes toward polypeptide-α-GalNAc-transferase T1 has been investigated. This study shows that this glycosyltransferase exhibits a very high substrate specificity.

Synthesis of amino-bridged oligosaccharide mimetics

Synthesis of amino-bridged oligosaccharides using reductive animation opens rapid access to novel glycomimetic target structures as potential ligands for the receptor protein NKR P1 of natural killer cells. Emphasis was laid on fast and facile synthetic routes. The carbonyl building blocks were easily obtained by oxidation with Dess-Martin periodinane or iodoxybenzoic acid (IBX). For the required amino-function-alized units, reduction of azide precursors was advantageous, and generation of the novel oligosaccharides was achieved by subsequent reductive amination. The target saccharide structures feature a bridging nitrogen atom inserted between two non-anomeric positions as well as including one anomeric position.

Synthesis of O-(2-O-sulfo-α-L-idopyranosyluronic acid)-(1 → 3)-2- acetamido-2-deoxy-4-O-sulfo-D-galactopyranose trisodium salt, a disaccharide fragment of dermatan sulfate

Benzyl 2-acetamido-2-deoxy-α, and β-D-glucopyranoside were converted in high yield into the corresponding D-galacto analogues through a three- step procedure. These later were transformed in a straightforward manner into benzyl 2-acetamido-4-O-acetyl-6-O-benzyl-2-deoxy-α, and β-D- galactopyranoside, respectively, which served as acceptors in glycosylation reactions with variously activated derivatives of methyl 2-O-benzoyl-3,O- benzyl-4-O-chloro-acetyl-L-idopyranuronate. Condensation of the chloride derivative promoted by silver triflate led unexpectedly to the formation of the β-linked disaccharide, whereas the trichloroacetimidoyl derivative afforded the expected α-linked disaccharide in 63% yield. O- Dechloroacetylation of this later, followed by 4-methoxybenzylation at O-4 of the uronic acid moiety, saponification of the esters, O-sulfonation of the free hydroxyls, and catalytic hydrogenation provided the title disaccharide in high yield, as its sodium salt.