87508-17-6

Basic information

• Product Name: PHENYL 4,6-O-BENZYLIDENE-1-THIO-BETA-D-GLUCOPYRANOSIDE
• Synonyms: PHENYL 4,6-O-BENZYLIDENE-1-THIO-BETA-D-GLUCOPYRANOSIDE;Phenyl 4,6-O-Benzylidene-1-thio-β-D-glucopyranoside;Phenyl 4,6-O-Benzylidene-1-thio-&beta
• CAS NO: 87508-17-6
• Molecular Formula: C₁₉H₂₀O₅S
• Molecular Weight: 360.42
• Product Categories: Glycosyl Donors;Biochemistry;Glucose;Sugars;Thioglycosides
• Mol File: 87508-17-6.mol
• Article Data: 41

Chemical Properties

• Melting Point: 185 °C
• Boiling Point: 581.153 °C at 760 mmHg
• Flash Point: 305.271 °C
• Appearance: /
• Density: 1.397 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: -45.5 ° (C=1, CHCl3)
• Storage Temp.: Freezer
• Solubility: slightly sol. in Chloroform
• CAS DataBase Reference: PHENYL 4,6-O-BENZYLIDENE-1-THIO-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYL 4,6-O-BENZYLIDENE-1-THIO-BETA-D-GLUCOPYRANOSIDE(87508-17-6)
• EPA Substance Registry System: PHENYL 4,6-O-BENZYLIDENE-1-THIO-BETA-D-GLUCOPYRANOSIDE(87508-17-6)

Safety Data

• Hazardous Substances Data: 87508-17-6(Hazardous Substances Data)

Usage

Description

Phenyl 4,6-o-benzylidene-1-thio-beta-d-glucopyranoside is a protected glucopyranoside that serves as a valuable building block for the synthesis of complex carbohydrates. It features β-phenylthio and 4,6-benzylidene protecting groups, which play a crucial role in the synthesis process.

Uses

Used in Carbohydrate Chemistry:
Phenyl 4,6-o-benzylidene-1-thio-beta-d-glucopyranoside is used as a building block for the synthesis of complex carbohydrates due to its protected structure. The β-phenylthio and 4,6-benzylidene protecting groups allow for selective reactions and controlled deprotection steps, facilitating the assembly of intricate carbohydrate structures.
Used in Pharmaceutical Industry:
Phenyl 4,6-o-benzylidene-1-thio-beta-d-glucopyranoside is used as an intermediate in the synthesis of pharmaceutical compounds, particularly those with carbohydrate-based structures. Its protected nature enables the development of novel drug candidates with potential therapeutic applications.
Used in Material Science:
In the field of material science, Phenyl 4,6-o-benzylidene-1-thio-beta-d-glucopyranoside can be used as a component in the design and synthesis of carbohydrate-based materials, such as polymers, gels, and coatings. These materials can exhibit unique properties and find applications in various industries, including biomedical, food, and environmental sectors.

InChI:InChI=1/C19H20O5S/c20-15-16(21)19(25-13-9-5-2-6-10-13)23-14-11-22-18(24-17(14)15)12-7-3-1-4-8-12/h1-10,14-21H,11H2/t14-,15-,16-,17-,18?,19+/m1/s1

Upstream product

• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 100-52-7 benzaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 108-98-5 thiophenol 
• 1203546-87-5 phenyl 2-O-acetyl-3-O-(azulen-1-yl-oxo-acetyl)-4,6-O-benzylidene-β-D-thiogalactopyranoside 
• 4163-60-4 β-D-galactose peracetate 
• 25878-60-8 D-galactose pentaacetate 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 618-31-5 benzylidene dibromide 
• 152983-23-8 phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 604-69-3 β-D-glucose pentaacetate 

Downstream Products

• 128848-54-4 phenyl 4,6-O-benzylidene-2,3-di-O-trimethylsilyl-1-thio-β-D-galactopyranoside 
• 128848-45-3 phenyl 4,6-O-benzylidene-2,3-di-O-trimethylsilyl-1-thio-β-D-glucopyranoside 
• 152983-24-9 phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 
• 152983-23-8 phenyl 2,3-di-O-acetyl-4,6-di-O-benzylidene-1-thio-β-D-glucopyranoside 
• 87470-70-0 S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thia-α-D-glucopyranoside 
• 124477-08-3 phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 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 
• 124477-09-4 Dithiocarbonic acid O-((2S,4aR,6S,7R,8S,8aS)-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl) ester S-methyl ester 
• 87470-72-2 phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 190367-07-8 phenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside 
• 131389-37-2 tert-Butyl-((2R,4aR,6S,7R,8S,8aR)-7-methoxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-dimethyl-silane 
• 201056-61-3 phenyl 2-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 175977-99-8 phenyl 6-O-benzyl-1-thio-β-D-galactopyranoside 

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.

Studies towards the total synthesis of repeating unit of O-sulfated polysaccharide from marine bacterium Cobetia pacifica KMM 3878

Herein we report assembly of the appropriately protected trisaccharide repeating unit of Cobetia pacifica KMM 3878 O-sulfated polysaccharide. Our synthesis involves 3,4-O-pyruvilated galactose as the key building block which acts as a donor as well as acceptor in the construction of trisaccharide. We obtained the R isomer as a major stereoisomer in the pyruvilation reaction. The glycosylations proceeded with high stereo and regioselectivity.

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.