165524-87-8

Upstream product

• 108-24-7 acetic anhydride 
• 100-39-0 benzyl bromide 
• 165524-85-6 6-O-(benzyl)-D-glucal 
• 13265-84-4 D-glucal 
• 145852-76-2 3,6-di-O-benzyl-D-glucal 

Downstream Products

• 187879-68-1 Acetic acid (2R,3S,4R,5R,6S)-5-benzenesulfonylamino-4-benzyloxy-6-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-2-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 4239-72-9 ethyl 2-acetamido-3,4,6-tetra-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 312967-20-7 ethyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 4229-38-3 2-acetamido-2-deoxy-β-D-glucopyranosylamine 
• 187879-75-0 N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-3-yl]-benzenesulfonamide 
• 187879-61-4 ethyl thioglycoside 

Relevant academic research and scientific papers

A highly convergent total synthetic route to glycopeptides carrying a high-mannose core pentasaccharide domain N-linked to a natural peptide motif

N-Linked glycopeptides were synthesized by condensation of a high-mannose anomeric amine bearing a pentasaccharide with aspartic-acid-containing tri- and pentapeptides through the agency of IIDQ. The pentasaccharide portion, corresponding to the 'core' re

Preparation of building blocks for carba-oligosaccharides: Some protected 5a′-carba-D-hexopyranosyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitols, and 5a,5a′-dicarba congeners thereof

Four configurational types of two protected O-linked (5a-carba-D- hexopyranosyl)-D-glucal and carba-D-glucal derivatives were prepared in order to provide versatile synthetic intermediates readily convertible into carba-oligosaccharides of biological inte

A highly convergent synthesis of an N-linked glycopeptide presenting the H-type 2 human blood group determinant

The total synthesis of an H-type blood group determinant in a model biological setting is described. The construct is comprised of a high mannose core structure with projecting lactose spacers, culminating in a two-copy presentation of the H-type blood group determinant itself. Key reactions that were used in this construction include sulfonamidohydroxylation (see 15→18) and benzoate-directed glycosylation via an activated thiophenyl donor (see 34→36). Another key strategic element involved the epimerization of an interior core glucoside to reach the β-mannoside (see 37→38) required in the ring C sugar of the high mannose core.

THE ALKYLATION AND ACYLATION OF GLYCALS VIA AN INITIALIZING ELECTROCHEMICAL STEP

The method of electrochemically induced formation of ether and ester derivatives of saturated mono- and disaccharides was applied to 1,2-unsaturated monosaccharides (D-glycals).The influence of the supporting electrolyte on the product distribution was investigated by variation of the cation.To provide data for comparison, alkylation was also carried out chemically in the presence of different bases, e.g.LiH and NaH.