183875-25-4

Upstream product

• 100-44-7 benzyl chloride 
• 261374-57-6 phenyl 1-thio-α-L-fucopyranoside 
• 100-39-0 benzyl bromide 
• 196397-53-2 phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-fucopyranoside 
• 127061-10-3 phenyl 2,3,4-tri-O-acetyl-1-thio-L-fucopyranoside 

Downstream Products

• 162118-38-9 (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 
• 876753-06-9 C₅₂H₆₇N₃O₆ 
• 876753-13-8 C₅₂H₆₇N₃O₆ 
• 1235577-60-2 C₅₉H₇₃N₃O₉ 
• 1250831-11-8 O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1→2)-O-(6-O-(4-chlorobenzoyl)-3,4-isopropylidene-β-D-galactopyranosyl)-(1→4)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal 
• 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 
• 424820-77-9 phenyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 220691-39-4 phenyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)-4-O-(acetyl-1-13C)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

From disulfide- to thioether-linked glycoproteins

(Chemical Presented) Strengthening the bond: The introduction of a thiol tag in combination with chemoselective ligation to form a disulfide-linked bioconjugate is a selective and useful method for site-selective protein glycosylation. The phosphine-mediated desulfurization of such glycoconjugates to their reductant-resistant thioether-linked counterparts completes a convergent, site-selective synthesis of thioether-linked glycoproteins (see scheme).

Direct one-pot conversion of acylated carbohydrates into their alkylated derivatives under heterogeneous reaction conditions using solid NaOH and a phase transfer catalyst

A convenient one-pot protocol for the direct conversion of acyl-protected carbohydrates into their alkylated counterparts has been developed by using alkyl halides in the presence of solid sodium hydroxide and a phase transfer catalyst. These economically

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.