167612-35-3

Usage

Uses

Used in Organic Chemistry:
Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside is used as a synthetic building block for the creation of various complex carbohydrate structures. Its unique structure allows chemists to introduce different functional groups and modify the molecule to suit specific applications.
Used in Biochemistry:
In the field of biochemistry, Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside is used as a key intermediate in the synthesis of asymmetric core-fucosylated and core-unmodified N-glycans. These glycans are essential components of various biological molecules, such as proteins and lipids, and play crucial roles in cellular recognition, signaling, and adhesion processes.
Used in Pharmaceutical Industry:
Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside is used as a starting material for the development of novel therapeutic agents targeting glycan-related diseases. The compound's ability to be modified and functionalized makes it an attractive candidate for the design of new drugs with improved efficacy and selectivity.
Used in Glycobiology Research:
In the field of glycobiology, Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside is used as a valuable tool for studying the structure, function, and biosynthesis of glycans. Researchers can use Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside to investigate the role of specific glycan structures in various biological processes and to develop new strategies for modulating glycan-mediated interactions.
Used in Drug Delivery Systems:
Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside can be employed in the development of targeted drug delivery systems. By incorporating Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside into the design of drug carriers, researchers can potentially enhance the specificity and efficacy of therapeutic agents by exploiting the unique interactions between glycans and their cognate receptors on target cells.

InChI:InChI=1/C33H34O4S/c1-25-30(34-22-26-14-6-2-7-15-26)31(35-23-27-16-8-3-9-17-27)32(36-24-28-18-10-4-11-19-28)33(37-25)38-29-20-12-5-13-21-29/h2-21,25,30-33H,22-24H2,1H3/t25-,30+,31-,32-,33+/m0/s1

Upstream product

• 187233-24-5 phenyl 6-deoxy-1-thio-β-L-galactopyranoside 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 73-34-7 6-deoxy-L-galactose 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 127061-10-3 phenyl 2,3,4-tri-O-acetyl-1-thio-L-fucopyranoside 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-β-L-fucopyranose 
• 167612-34-2 phenyl 6-deoxy-2,3,4-tri-O-acetyl-1-thio-β-L-galactopyranoside 
• 108-98-5 thiophenol 

Downstream Products

• 271248-87-4 C₆₉H₇₀N₂O₂₀ 
• 33639-74-6 (2R,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran 
• 851321-42-1 2-{6-(2-azido-ethoxy)-8-[4,5-bis-benzyloxy-6-benzyloxymethyl-3-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-isoindole-1,3-dione 
• 904666-14-4 C₅₄H₅₇FO₉ 
• 904895-06-3 phenyl 4,7-di-O-acetyl-5-amino-9-O-benzyl-3,5-dideoxy-2-thio-8-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-D-glycero-α-D-galacto-2-nonulopyranoside-1,5-lactam 
• 953780-99-9 tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide 

Relevant academic research and scientific papers

Kilogram scale chemical synthesis of 2′-fucosyllactose

A scalable synthetic procedure to high quality 2′-fucosyllactose, the most abundant oligosaccharide in human breast milk, has been designed and validated in kilogram scale. The synthetic route has been developed to suit industrial environment and contains

METHOD FOR THE SYNTHESIS OF A TRISACCHARIDE

The present invention relates to an improved synthesis of a trisaccharide of the formula (1), novel intermediates used in the synthesis and the preparation of the intermediates.

SYNTHESIS OF 2'-O-FUCOSYLLACTOSE

The present invention relates to an improved synthesis of a trisaccharide of the formula (1), novel intermediates used in the synthesis and the preparation of the intermediates.

Preparation of Thiosugars and Their Use

A process for the preparation of a thiosaccharide represented by Saccharide-S-H wherein Saccharide comprises at least 4 sugar units, comprises subjecting a corresponding compound of the formula (P)Saccharide-S-(P) wherein (P) represents an O- or S-protecting group(s), to Birch reduction.

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).

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.

Synthesis and biological evaluation of a new sialyl Lewis X mimetic derived from lactose

A sialyl Lewis X (sLex) mimetic compound, 2-(trimethylsilyl)ethyl 3-O-carboxymethyl-β-D-galactopyranosyl-(1→4)-[α-L-fucosyl- (1→6)]-β-D-glucopyranoside (2a), has been synthesized in 14 steps from D-lactose. This synthesis features the use of the activated glycosylating donor, lactosyl iodide, in a Koenigs-Knorr sequence, the regioselective derivatization at the C-3 position of the galactose moiety, and the stereoselective construction of a fucose-α(1→6)-lactose linkage. The mimetic was tested for its ability to inhibit human polymorphonuclear leukocyte (hPMNL) adhesion to immobilized recombinant human E-selectin under shear stress conditions.

Sulfated and phosphated saccharide derivatives, process for the preparation of the same and use thereof

There are described sulfated and phosphated saccharide erivatives of the Formula STR1 wherein R1 is hydrogen atom or a residue of sulfate, phosphate or L-fucose; R2, R3 and R4 are hydrogen atom or a residue of sulfate or phosphate, respectively; 1 is an integer of 0 or 1; m is an integer of 0-15; and n is an integer of 0-21, or pharmaceutically acceptable salts thereof, a process for the preparation of the derivatives and salts as well as use thereof, as an anti-inflammatory agent.

Synthesis and biological activities of three sulfated sialyl Le(x) ganglioside analogues for clarifying the real carbohydrate ligand structure of L-selectin

Sulfated sialyl Le(x) ganglioside analogues at C-6 of D-galactose, N-acetyl-D-glucosamine, and of both D-galactose and N-acetyl-D-glucosamine residues have been synthesized, in order to clarify the structure of the real carbohydrate ligand of L-selectin. Coupling of the suitably protected N-acetyl-D-glucosaminyl-β(1→3)-lactose derivatives 13 and 16 with the sialyl α(2→3)-D-galactopyranosyl trichloroacetimidates 10 and 12 (glycosyl donors), via glycosylation of 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-galactopyranoside (1) with the phenyl 2-thioglycoside derivative (2) of N-acetylneuraminic acid (Neu5Ac) using N-iodosuccinimide/TfOH, O-benzoylation, removal of the benzylidene group affording 5, selective 6-O-levulinoylation, O-benzoylation, removal of the 2-(trimethylsilyl)ethyl group, and imidate formation, or via O-acetylation of 5, removal of the 2-(trimethylsilyl)ethyl group, then imidate formation, gave the pentasaccharides 18-20. The glycosylation of the pentasaccharide accepters (21-23) derived from 18-20 by removal of the 4-methoxybenzyl group, with phenyl 1-thioglycoside derivative 27 of L-fucose using dimethyl(methylthio)sulfonium triflate (DMTST) afforded the corresponding hexasaccharides 28-30, which were transformed in good yields, via reductive removal of their benzyl groups, O-acetylation, selective removal of the 2-(trimethylsilyl)ethyl group, imidate formation, coupling with (2S,3R,4E)-2-azido-O-benzoyl-4-octadecene-1,3-diol (35) in the presence of boron trifluoride etherate, selective reduction of the azido group, coupling with octadecanoic acid, selective removal of the levulinoyl groups, treatment with sulfur trioxide-pyridine complex, then removal of the protecting groups, into the desired sulfated sialyl Le(x) ganglioside analogues 50-52.