895140-55-3

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 129750-23-8 Ethyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 80065-87-8 1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside 
• 28140-37-6 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside 
• 13242-53-0 acetobromomannose 
• 83-87-4 D-Mannose pentaacetate 
• 32860-96-1 3,4,6-tri-O-benzyl-1,2-O-(1-ethoxyethylidene)-β-D-mannopyranoside 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 75-08-1 ethanethiol 
• 130525-72-3 ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 16697-49-7 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose 

Downstream Products

• 199116-19-3 C₈₀H₁₀₂O₁₅Si₂ 

Relevant academic research and scientific papers

Synthesis of Azido-Glycans for Chemical Glycomodification of Proteins

Chemically produced, accurately linkable oligosaccharides are of importance for the synthesis of neo-glycoproteins. On the route to high-mannose type N-glycans, we present a convenient synthesis of several glycans bearing an azide moiety at the reducing end. An azido-glycan core structure as valuable precursor was modified into the protected N-glycan pentasaccharide core structure and the possibility of modular attachment of different antenna was demonstrated through synthesis of a pentamannose donor and glycosylation with the core structure. The azido function allows for chemical ligation with recombinantly modified proteins featuring noncanonical cyclooctyne amino acids, providing access to customized glycopatterns of glycoproteins, e.g., of antibodies that are of high interest for biopharmaceutical applications.

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.