138922-03-9

Basic information

• Product Name: Phenyl 4,6-O-benzylidene-bD-thiogalactopyranoside
• Synonyms: Phenyl 4,6-O-benzylidene-bD-thiogalactopyranoside;Phenyl 4,6-O-(phenylmethylene)-1-thio-beta-D-galactopyranoside
• CAS NO: 138922-03-9
• Molecular Formula: C₁₉H₂₀O₅S
• Molecular Weight: 360.4241
• Mol File: 138922-03-9.mol
• Article Data: 51

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Phenyl 4,6-O-benzylidene-bD-thiogalactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl 4,6-O-benzylidene-bD-thiogalactopyranoside(138922-03-9)
• EPA Substance Registry System: Phenyl 4,6-O-benzylidene-bD-thiogalactopyranoside(138922-03-9)

Safety Data

• Hazardous Substances Data: 138922-03-9(Hazardous Substances Data)

Usage

Description

Phenyl 4,6-O-benzylidene-bD-thiogalactopyranoside is a chemical compound that belongs to the class of thiogalactopyranosides. It is characterized by the presence of a benzylidene group that plays a crucial role in stabilizing the compound and protecting it from degradation. Phenyl 4,6-O-benzylidene-bD-thiogalactopyranoside holds significant biochemical and pharmacological importance, making it a valuable asset in both industrial and academic settings.

Uses

Used in Biochemical Research:
Phenyl 4,6-O-benzylidene-bD-thiogalactopyranoside is used as a substrate for measuring the activity of enzymes such as beta-galactosidase. This application is crucial for studying enzyme kinetics and understanding the mechanisms of enzymatic reactions.
Used in Pharmaceutical Research:
In the pharmaceutical industry, Phenyl 4,6-O-benzylidene-bD-thiogalactopyranoside serves as a key component in the development of new drugs. Its unique structure and properties make it a promising candidate for the creation of innovative therapeutic agents.
Used in the Synthesis of Glycosidic Compounds:
Phenyl 4,6-O-benzylidene-bD-thiogalactopyranoside is also utilized in the synthesis of various glycosidic compounds. Its role in this process is vital for the production of complex carbohydrate structures that are essential in numerous biological processes.
Used in Academic Settings:
Phenyl 4,6-O-benzylidene-bD-thiogalactopyranoside is employed in academic research to explore its potential applications and to further understand its biochemical properties. This research contributes to the advancement of scientific knowledge and the development of new technologies in the field of biochemistry.

Upstream product

• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 100-52-7 benzaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside 
• 604-68-2 α-D-glucopyranose peracetylate 
• 108-98-5 thiophenol 
• 13992-16-0 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 13992-15-9 phenyl-1-thio-α-D-glucopyranoside 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 4163-60-4 β-D-galactose peracetate 
• 144830-21-7 phenyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 
• 231623-55-5 phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranoside 
• 911684-18-9 phenyl 4,6-di-O-acetyl-2,3-di-O-benzyl-1-thio-β-D-galactopyranoside 
• 774-48-1 (diethoxymethyl)benzene 

Downstream Products

• 179072-68-5 phenyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside 
• 688315-42-6 phenyl 4,6-O-benzylidene-3-O-{[(1-ethylpropyl)(9H-fluoren-9-ylmethoxycarbonyl)amino]acetyl}-1-thio-β-D-galactopyranoside 
• 213997-89-8 phenyl 3-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 804566-04-9 phenyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 128848-45-3 phenyl 4,6-O-benzylidene-2,3-di-O-trimethylsilyl-1-thio-β-D-glucopyranoside 
• 152983-23-8 phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-glucopyranoside 
• 128848-51-1 phenyl 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside 
• 87470-70-0 S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside 
• 213997-99-0 phenyl 4,6-O-benzylidene-3-O-pivaloyl-1-thio-β-D-glucopyranoside 
• 685136-14-5 phenyl 2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 942622-12-0 phenyl 4,6-O-benzylidene-3-O-methoxymethyl-1-thio-β-D-glucopyranoside 
• 322472-81-1 phenyl 4,6-O-benzylidene-2-O-pentyl-1-thio-β-D-glucopyranose 
• 322472-82-2 phenyl 4,6-O-benzylidene-2,3-di-O-pentyl-1-thio-β-D-glucopyranose 
• 201056-61-3 phenyl 2-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 

Relevant articles and documents

N -Glycosylation with sulfoxide donors for the synthesis of peptidonucleosides

The synthesis of glycopyranosyl nucleosides modified in the sugar moiety has been less frequently explored, notably because of the lack of a reliable method to glycosylate pyrimidine bases. Herein we report a solution in the context of the synthesis of peptidonucleosides. They were obtained after glycosylation of different pyrimidine nucleobases with glucopyranosyl donors carrying an azide group at the C4 position. A methodological study involving different anomeric leaving groups (acetate, phenylsulfoxide and ortho-hexynylbenzoate) showed that a sulfoxide donor in combination with trimethylsilyl triflate as the promoter led to the best yields.

Total Synthesis of the Echinodermatous Ganglioside LLG-3 Possessing the Biological Function of Promoting the Neurite Outgrowth

A total synthesis of echinodermatous ganglioside LLG-3 with neuritogenic activity was accomplished by a convergent strategy. The synthesis of 2-hydroxyethyl 8-O-Me-α-sialoside 2 was started from the phenyl 7,8-di-O-Pico-thiosialoside 5, which can be chemoselectively removed the picoloyl group, and then the methyl group in 8-O-MeNeu5Ac moiety was chemoselectively prepared using TMSCHN2/FeCl3. For preparation of the terminal disialic unit, oxidative amidation was initially utilized by our group to efficiently construct the α(2,11) linkage of 8-O-Me-Neu5Acα(2,11)Neu5Gc. Herein, we also demonstrate that the synthesized ganglioside LLG-3 exhibited the neuritogenic activity toward the primary cortical neurons and that biological activity is superior to that of ganglioside DSG-A.

Molecular-Level Understanding of the Major Fragmentation Mechanisms of Cellulose Fast Pyrolysis: An Experimental Approach Based on Isotopically Labeled Model Compounds

Evaluation of the feasibility of various mechanisms possibly involved in cellulose fast pyrolysis is challenging. Therefore, selectively 13C-labeled cellotriose, 18O-labeled cellobiose, and 13C- and 18O-doubly-labeled cellobiose were synthesized and subjected to fast pyrolysis in an atmospheric pressure chemical ionization source of a linear quadrupole ion trap/orbitrap mass spectrometer. The initial products were immediately quenched, ionized using ammonium cations, and subsequently analyzed using the mass spectrometer. The loss or retention of isotope labels upon pyrolysis unambiguously revealed three major competing mechanisms - sequential losses of glycolaldehyde/ethenediol molecules from the reducing end (the reducing-end unraveling mechanism), hydroxymethylene-assisted glycosidic bond cleavage (HAGBC mechanism), and Maccoll elimination. Important discoveries include the following: (1) Reducing-end unraveling is the predominant mechanism occurring at the reducing end; (2) Maccoll elimination facilitates the cleaving of aglyconic bonds, and it is the mechanism leading to formation of reducing carbohydrates; 3) HAGBC occurs for glycosides but not at the reducing end of cellodextrins; 4) HAGBC and water loss are the predominant reactions for fast pyrolysis of 1,6-anhydrocellodextrins; and 5) HAGBC can proceed after reducing-end unraveling but unraveling does not occur once the HAGBC reaction pathway is initiated. Moreover, hydrolysis was conclusively ruled out for fast pyrolysis of cellobiose, cellotriose, and 1,6-anhydrocellodextrins up to cellotetraosan. No radical reactions were observed.