183875-25-4

Basic information

• Product Name: phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside
• Synonyms: phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside
• CAS NO: 183875-25-4
• Molecular Weight: 526.697
• Mol File: 183875-25-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside(183875-25-4)
• EPA Substance Registry System: phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside(183875-25-4)

Safety Data

• Hazardous Substances Data: 183875-25-4(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 176106-81-3 Galβ1-4(Fucα1-3)GlcNAcβ1-OMe 
• 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 
• 183875-09-4 C₅₈H₆₉N₃O₁₈S 
• 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 
• 1235577-60-2 C₅₉H₇₃N₃O₉ 
• 876753-06-9 C₅₂H₆₇N₃O₆ 
• 876753-13-8 C₅₂H₆₇N₃O₆ 
• 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 
• 162118-38-9 (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 

Relevant articles and documents

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).

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.