84635-54-1

Usage

Uses

Used in Scientific Research:
METHYL 2,3,4-TRI-O-ACETYL-1-THIO-BETA-L-FUCOPYRANOSIDE is used as a research compound for studying biological processes and understanding the role of fucose in physiological and pathological processes such as cancer metastasis and inflammation. Its sulphide and acetate groups contribute to its interactions, making it a valuable tool in scientific investigations.

InChI:InChI=1/C13H20O7S/c1-6-10(18-7(2)14)11(19-8(3)15)12(20-9(4)16)13(17-6)21-5/h6,10-13H,1-5H3/t6-,10+,11+,12-,13+/m0/s1

Upstream product

• 3908-55-2 Trimethyl(methylthio)silane 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 17314-32-8 tributyl(methylthio)stannane 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-β-L-fucopyranose 
• 56981-44-3 (2R,3S,4R,5R,6S)-2-mercapto-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 74-88-4 methyl iodide 
• 624-92-0 Dimethyldisulphide 
• 793696-65-8 2,3,4-tri-O-acetyl-α-L-fucopyranosyl iodide 
• 73-34-7 6-deoxy-L-galactose 
• 80483-13-2 2,3,4-tri-O-acetyl-L-fucopyranosyl bromide 
• 7404-35-5 2,3,4-tri-O-acetyl-α/β-L-fucopyranosyl acetate 
• 108-24-7 acetic anhydride 
• 114853-38-2 methyl 1-thio-β-L-fucopyranoside 

Downstream Products

• 114853-38-2 methyl 1-thio-β-L-fucopyranoside 
• 157865-35-5 methyl 2,3,4-tri-O-(4-methoxybenzyl)-1-thio-β-L-fucopyranoside 
• 186967-60-2 C₅₅H₇₆O₂₀ 
• 107802-80-2 (2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran 
• 1756-21-4 (2R,3S,4R,5S,6S)-2-Methyl-6-methylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 114853-30-4 O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 107802-80-2 methyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 
• 107802-81-3 allyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-O-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)>-6-O-benzyl-2-deoxy-2-phtalimido-β-D-glucopyranoside 
• 107802-83-5 O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 
• 16741-27-8 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide 

Relevant academic research and scientific papers

New method for regioselective glycosylation employing saccharide oxyanions

As an alternative concept for glycosylation, the prior activation of acceptor hydroxy groups for selective glycosidic bond formation, was investigated to give complex oligosaccharides. Oxyanions obtained from partially protected saccharides were glycosylated by employing glycopyranosyl halides, and the regiochemical results were studied. Initially, partially methylated methyl-α-D-glucopyranosides were used as a model system to study the underlying mechanistic principles of base-promoted glycosylation. High regioselectivities and stereospecific glycosidic bond formations were achieved, and the scope of the methodology was extended with different perbenzylated glycosyl donors.

Streamlined synthesis of per-O-acetylated sugars, glycosyl iodides, or thioglycosides from unprotected reducing sugars

Solvent-free per-O-acetylation of sugars with stoichiometric acetic anhydride and catalytic iodine proceeds in high yield (90-99%) to give exclusively pyranose products as anomeric mixtures. Without workup, subsequent anomeric substitution employing iodine in the presence of hexamethyldisilane (i.e., TMS-I generated in situ) gives the corresponding glycosyl iodides in 75-95% isolated yield. Alternatively, and without workup, further treatment with dimethyl disulfide or thiol (ethanethiol or thiocresol) gives anomerically pure thioglycosides in more than 75% overall yield.

Synthesis of α-D-Manp-(1->3)-4)>-6)>-β-D-Manp-(1->4)-β-D-GlcpNAc-(1->4)-6)>-D-GlcpNAc, a core glycoheptaose of a "bisected" complex-type glycan of glycoproteins

A synthesis of α-D-Manp-(1->3)-4)>-6)>-β-D-Manp-(1->4)-β-D-GlcpNAc-(1->4)-6)>-D-GlcpNAc was achieved by employing benzyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-O-(2-O-benzyl-β-D-

Synthesis of the sodium salts of methyl 2-O-alpha-L-fucopyranosyl-alpha-L-fucopyranoside 3- and 4-sulfate.

Synthesis of methyl 2-O-alpha-L-fucopyranosyl-alpha-L-fucopyranoside 3- and 4-sulfate was accomplished through the use of a key glycosyl donor, methyl 2,3,4-tri-O-benzyl-1-thio-beta-L-fucopyranoside, with methyl 2,3-O-isopropylidene-alpha-L-fucopyranoside and methyl 4-O-acetyl-3-O-benzyl-alpha-fucopyranoside as acceptors.

Total synthesis of X hapten, III3 Fuc alpha-nLc4 Cer.

Total synthesis of O-beta-D-galactopyranosyl-(1----4)-O-[alpha-L- fucopyranosyl- (1----3)]-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----3)-O-beta- D- galactopyranosyl- (1----4)-O-beta-D-glucopyranosyl-(1----1)-2-N-tetracosanoyl-(2S,3R ,4E)- sphinge

A Through-process for the Preparation of Methyl Per-O-acetyl 1-Thio-glycosides from Aldoses

D-Glucose, D-galactose, D-mannose, D-xylose, L-arabinose, L-fucose, L-rhamnose, maltose, cellobiose, lactose, D-glucosamine, D-galactosamine, and D-mannosamine were converted into the corresponding methyl per-O-acetyl 1-thioglycopyranosides by way of a three-step (acetobromination, methylthioation, and acetylation) through-process in a single vessel.