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

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

Downstream Products

• 1193784-34-7 phenyl 2-O-acetyl-4,6-O-benzylidene-1-thio-3-O-trifluoromethanesulfonyl-β-D-galactopyranoside 
• 1185735-67-4 phenyl 2-O-acetyl-4,6-O-benzyliden-1-thio-β-D-gulopyranoside 
• 1185735-68-5 phenyl 2-O-acetyl-4,6-O-benzylidene-1-thio-3-O-trifluoromethanesulfonyl-β-D-gulopyranoside 
• 1185735-69-6 phenyl 2-O-acetyl-3-azido-4,6-O-benzylidene-3-deoxy-1-thio-β-D-galactopyranoside 
• 1193784-35-8 phenyl 2-O-acetyl-3-azido-3-deoxy-1-thio-β-D-galactopyranoside 
• 1193784-36-9 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-4-azido-6-(phenylthio)tetrahydro-2H-pyran-3,5-diyl diacetate 
• 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 

Relevant articles and documents

Studies of Catalyst-Controlled Regioselective Acetalization and Its Application to Single-Pot Synthesis of Differentially Protected Saccharides

This article describes studies on the regioselective acetal protection of monosaccharide-based diols using chiral phosphoric acids (CPAs) and their immobilized polymeric variants, (R)-Ad-TRIP-PS and (S)-SPINOL-PS, as the catalysts. These catalyst-controll

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.

Conformationally Switchable Glycosyl Donors

Glycosyl donors functionalized with 2,2′-bipyridine moieties on the 3-OH and 6-OH or the 2-OH and 4-OH undergo a conformational change when forming 1:1 complexes with Zn2+ ions. The pyranoside ring of the zinc complexes adopted axial-rich skew boat conformations. The reactivities of the two glycosyl donors were investigated by performing a series of glycosylations in the presence or absence of Zn2+ ions. These glycosylations suggested a decrease in reactivity when binding Zn2+. The conformational effect of binding Zn2+ was therefore studied using a third glycosyl donor, unable to undergo conformational changes when binding Zn2+. From competition experiments, it was observed that the binding-induced conformational change increased the reactivity slightly compared to the glycosyl donor unable to undergo a conformational change.