117467-63-7

Upstream product

• 108-24-7 acetic anhydride 
• 1398-61-4 chitin 
• 55682-57-0 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 109898-90-0 2-Acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-mannopyranosyl)-1,6-di-O-acetyl-3-O-benzyl-2-desoxy-α-D-glucopyranose 
• 95451-93-7 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl bromide 
• 77735-20-7 Acetic acid (2R,3S,4R,5R,6S)-6-acetoxy-5-acetylamino-3-((2S,3S,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester 

Downstream Products

• 19272-52-7 benzyl 2-acetylamino-4-O-(2-acetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside 
• 17188-78-2 benzyl 2-acetamido-4-O-(2'-acetamido-2'-deoxy-3',4',6'-tri-O-acetyl-β-D-glucopyranosyl)-2-deoxy-3,6-di-O-acetyl-β-D-glucopyranoside 
• 79365-98-3 6-O-α-L-fucopyranosyl-di-N-acetylchitobiose 
• 129579-88-0 benzyl 2-acetamido-4-O-(2'-acetamido-4',6'-O-benzylidene-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside 
• 129579-89-1 benzyl 2-acetamido-4-O-(2'-acetamido-4',6'-benzylidene-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(2'',3'',4''-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

Improving glycopeptide synthesis: A convenient protocol for the preparation of β-glycosylamines and the synthesis of glycopeptides

(Chemical Equation Presented) Herein we apply a recently introduced protocol using ammonium carbamate in methanol to the amination of crude chitobiose leading to 1,β-aminochitobiose. This simple, one-step procedure allows a facile preparation of unstable glycosylamines in contrast to the commonly implemented ammonium bicarbonate based amination of water-soluble carbohydrates. The new amination protocol leads to an improved synthesis of the key chitobiosyl-asparagine building block for the SPPS of glycopeptides. The utility of the method is demonstrated with the synthesis of a 39-amino acid glycoprotein.

Synthesis of trisaccharide determinants of enterobacterial common antigens

In the presence of silver silicate, the reaction of 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-mannopyranosyl bromide with 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-beta-D-glucopyranose gave beta-glycosidically linked 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-4-O-(3,4,6- tri-O-acetyl-2-azido-2-deoxy-beta-D-mannopyranosyl)-beta-D- glucopyranose. After deacetylation and catalytic oxidation with oxygen and platinum, 1,6-anhydro-2-azido-4-O-[(2-azido-2-deoxy-beta-D-mannopyranosyl) uronic acid]-3-O-benzyl-2-deoxy-beta-D-glucopyranose was obtained. A series of intermediate steps led to the glycosyl donor 6-O-acetyl-2-azido-3-O-benzyl-4-O-[benzyl (3,4-di-O-acetyl-2-azido-2-deoxy-beta-D-mannopyranosyl)uronate]-2-deoxy- alpha, beta-glucopyranosyl chloride which was coupled with 8-methoxycarbonyloctyl 4-azido-2-O-benzyl-4,6-dideoxy-alpha-D-galactopyranoside to give 8-methoxycarbonyloctyl O-[benzyl (3,4-di-O-acetyl-2-azido-2-deoxy-beta-D-mannopyranosyl)uronate]- (1----4)-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-alpha-D-glucopyranosyl )-(1----3)-4-azido-2-O-benzyl-4,6-dideoxy-alpha-D-galactopyranoside. Deblocking gave the spacer-linked repeating unit of the enterobacterial common antigen, beta-D-ManpNAcA-(1----4)-alpha-D-GlcpNAc-(1----3)-alpha- D-Fucp4NACO(CH2)8CO2CH3.