157135-66-5

Upstream product

• 167612-35-3 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 
• 100-39-0 benzyl bromide 
• 196397-53-2 phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-fucopyranoside 
• 261374-57-6 phenyl 1-thio-α-L-fucopyranoside 
• 100-44-7 benzyl chloride 
• 187233-24-5 phenyl 6-deoxy-1-thio-β-L-galactopyranoside 
• 183875-25-4 phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside 

Downstream Products

• 183875-09-4 C₅₈H₆₉N₃O₁₈S 
• 183875-20-9 Acetic acid (2R,3S,4R,5R,6R)-5-azido-6-phenylsulfanyl-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester 
• 176106-81-3 Galβ1-4(Fucα1-3)GlcNAcβ1-OMe 

Relevant academic research and scientific papers

Control of disaccharide conformation by π-stacking

The conformations of a series of derivatives of the disaccharide α-L-fucopyranosyl-(1→3)-2-acetamido-2-deoxy-D-glucopyranoside, part of the Lex determinant, were studied by molecular modelling using the MM3* forcefield and by 1H NMR spectroscopy. Unusually shielded O- benzyl protons were observed in the 1H NMR spectrum of phenyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1→3)- 2-deoxy-2-phthalimido-1-thio-α-D-glucopyranoside and assigned to the 2-O-benzyl group. This observation was explained by a shift in the population of the conformational mixture present about the glycosidic linkage from the positive Ψ region in the unsubstituted disaccharide to the negative Ψ region induced by π-stacking between the phthalimide and the 2-O-benzyl phenyl ring. The experimental nuclear Overhauser enhancements confirm the accuracy of the calculations.

Generalizing glycosylation: Synthesis of the blood group antigens Lea, Leb, and Le(x) using a standard set of reaction conditions

Because there are no general reaction conditions for any glycosylation method, biologically interesting oligosaccharides can only be made in a small number of laboratories in the world. To make carbohydrate synthesis accessible to nonspecialists, it is critical to have glycosylation methods that will work in a wide range of cases under a single set of conditions. The Lewis blood group antigens have attracted the attention of numerous synthetic carbohydrate groups because of their structural complexity. Although they have been synthesized many times, they have never been made using a single glycosylation method under one set of reaction conditions. In this paper, we show that the sulfoxide glycosylation method can be used to form all of the glycosidic linkages in the Lewis blood group antigens Lea (1), Leb (2), and Le(x) (3) stereoselectively under a uniform set of reaction conditions. This work highlights the flexibility of the sulfoxide method and demonstrates its utility for constructing families of related oligosaccharides.