127061-08-9

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSYL FLUORIDE is used as a building block for the synthesis of complex carbohydrates and glycoconjugates, which are essential in the development of new drugs targeting various diseases. The selective manipulation of the molecule during chemical reactions allows for the creation of diverse carbohydrate structures with potential therapeutic applications.
Used in Biochemical Research:
In biochemical research, 2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSYL FLUORIDE serves as a valuable tool for studying the structure and function of carbohydrates and their interactions with proteins and other biomolecules. 2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSYL FLUORIDE's ability to form diverse carbohydrate structures enables researchers to investigate the role of glycosylation in biological processes and disease mechanisms.
Used in Glycoconjugate Synthesis:
2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSYL FLUORIDE is used as a key intermediate in the synthesis of glycoconjugates, which are compounds consisting of a carbohydrate moiety covalently linked to a non-carbohydrate moiety, such as a protein or lipid. These glycoconjugates play crucial roles in various biological processes, including cell recognition, signal transduction, and immune response. 2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSYL FLUORIDE's protective benzyl groups and activated anomeric carbon facilitate the synthesis of these complex structures for research and therapeutic purposes.

Upstream product

• 162118-38-9 (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 
• 169532-17-6 ethyl 2,3,4-tri-O-benzyl-1-thio-α/β-L-fucopyranoside 

Downstream Products

• 142800-29-1 (2R,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-((3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-3-ol 
• 136514-62-0 C₆₈H₇₇NO₁₈ 
• 138407-74-6 (-)-O-<2,3,4-tri-O-benzyl-α-L-fucopyranosyl>-(1<*>3)-1,5-anhydro-4-O-acetyl-2-deoxy-5(S)-phenyl-L-xylo-pent-1-enopyranose 
• 138407-74-6 O-<2,3,4-tri-O-benzyl-β-L-fucopyranosyl>-(1<*>3)-1,5-anhydro-4-O-acetyl-2-deoxy-5(S)-phenyl-L-xylo-pent-1-enopyranose 
• 152932-86-0 C₆₈H₇₀ClNO₁₉S 
• 162128-81-6 C₈₅H₁₁₄O₁₈Si₂ 
• 162128-74-7 (3aS,4R,6S,7R,7aS)-6-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-4-triisopropylsilanyloxymethyl-7-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one 
• 165816-42-2 C₅₈H₈₆O₁₄Si₂ 
• 190587-45-2 N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-seryl-D-glutamic acid 1-methylamide 5-benzyl ester 
• 190587-44-1 -L-glutamic acid 1-methylamide 5-benzyl ester 
• 190587-43-0 N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-L-seryl-D-glutamic acid 1-methylamide 5-benzyl ester 
• 190587-42-9 N-(tert-butoxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-L-seryl-L-glutamic acid 1-methylamide 5-benzyl ester 
• 200003-52-7 allyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-4,6-O-benzylidene)-β-D-glucopyranoside 
• 200003-37-8 allyl (2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3[2-O-benzyl-4,6-O-(4-methoxy)benzylidene]-β-D-glucopyranoside 

Relevant academic research and scientific papers

Total synthesis of a sialyl Lewisx derivative for the diagnosis of cancer

The total synthesis of aminoethyl glycoside of sialyl Lewisx (sLex) is described. A galactose donor was condensed with a diol of glucosamine to afford regioselectively a β1,4 linked disaccharide, which was further stereoselectively fucosylated to provide a protected Lewis x trisaccharide. After chemical modification, the trisaccharide was sialylated to give regio- and stereoselectively an azidoethyl glycoside of sLex. Finally, deprotection and azide reduction afforded the target compound. This compound will be coupled with protein and then be used to conduct further preclinical studies for the diagnosis of cancer.

Synthesis of biologically active sialyl Lewis X mimetics

The design and synthesis of two sialyl Lewis X (SLe(x)) mimetics are described. In the design of mimetic 1, an ethylene glycol linkage is used to bridge the fucose and galactose moiety, and a carboxymethyl group is placed in the 3-OH position of the galactose residue to provide the negative charge which is believed to be essential for binding to (E)-selectin. In the design of mimetic 2, a D-tartaric acid derivative is used to provide the trans-dihydroxyl groups originally from the glucosamine moiety for the linkage of the fucose and the carboxypentyl groups. At a concentration of 1.5 mM, 1 inhibits 50% of the binding of SLe(x) glycoconjugate to immobilized recombinant (E)-selectin, while 2 has an IC50 of 10 mM. Mimetic 1 is also found to be stable toward α-L-fucosidase. Results from the ROESY and COSY experiments indicate that compound 1 is conformationally flexible, which may explain its relatively weak activity compared to SLe(x) (IC50 = 0.8 mM).