167612-35-3

Basic information

• Product Name: Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside
• Synonyms: Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside;Phenyl 2,3,4-Tri-O-benzyl-1-thio-β-L-fucopyranoside;Phenyl 2,3,4-Tri-O-benzyl-1-thio-&beta
• CAS NO: 167612-35-3
• Molecular Formula: C₃₃H₃₄O₄S
• Molecular Weight: 526.68566
• Mol File: 167612-35-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 106.0 to 110.0 °C
• Boiling Point: 644.498°C at 760 mmHg
• Flash Point: 343.58°C
• Appearance: /
• Density: 1.205g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.63
• CAS DataBase Reference: Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside(167612-35-3)
• EPA Substance Registry System: Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside(167612-35-3)

Safety Data

• Hazardous Substances Data: 167612-35-3(Hazardous Substances Data)

Usage

Description

Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside, with the CAS number 167612-35-3, is a synthetic carbohydrate derivative that plays a significant role in the field of organic chemistry and biochemistry. It is characterized by its unique structure, which features a phenyl group and three benzyl groups attached to a thio-beta-L-fucopyranoside core. Phenyl 2,3,4-Tri-O-benzyl-1-thio-beta-L-fucopyranoside is particularly valuable for its ability to be used in the synthesis of complex carbohydrate structures, such as asymmetric core-fucosylated and core-unmodified N-glycans.

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 this compound 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 this compound 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

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

Downstream Products

• 271248-87-4 C₆₉H₇₀N₂O₂₀ 
• 157135-66-5 phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranosyl sulfoxide 
• 953780-99-9 tri-O-benzyl-α-L-fucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranosyl azide 
• 639507-67-8 phenyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-1-thio-β-L-glucopyranoside 
• 182195-47-7 1-Benzyloxymethyl-9-[(2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one 
• 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 
• 33639-74-6 (2R,3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran 

Relevant articles and documents

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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

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.

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).