187879-75-0

Upstream product

• 187879-61-4 ethyl thioglycoside 
• 187879-55-6 Acetic acid (2R,3R,4S,5S,6S)-6-benzenesulfonylamino-4-benzyloxy-2-benzyloxymethyl-5-iodo-tetrahydro-pyran-3-yl ester 
• 165524-87-8 4-O-acetyl-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol 
• 145852-76-2 3,6-di-O-benzyl-D-glucal 
• 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 

Relevant academic research and scientific papers

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.

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