56119-28-9

Basic information

• Product Name: Ethyl4,6-O-benzylidene-b-D-thiogalactopyranoside
• Synonyms: Ethyl4,6-O-benzylidene-b-D-thiogalactopyranoside;Ethyl 4, 6-O-benzylidene-thio-b-D-galactoside;Ethyl 4,6-O-benzylidene-thio-beta-D-galactoside
• CAS NO: 56119-28-9
• Molecular Formula: C₁₅H₂₀O₅S
• Molecular Weight: 312.38
• Mol File: 56119-28-9.mol
• Article Data: 26

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethyl4,6-O-benzylidene-b-D-thiogalactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl4,6-O-benzylidene-b-D-thiogalactopyranoside(56119-28-9)
• EPA Substance Registry System: Ethyl4,6-O-benzylidene-b-D-thiogalactopyranoside(56119-28-9)

Safety Data

• Hazardous Substances Data: 56119-28-9(Hazardous Substances Data)

Usage

General Description

Ethyl 4,6-O-benzylidene-β-D-thiogalactopyranoside is a chemical compound that is commonly used as a substrate for studying the enzymatic hydrolysis of glycosidic bonds. It is a thioglycoside derivative of galactose, and its benzylidene group is often used to protect the hydroxyl groups of the sugar. Ethyl4,6-O-benzylidene-b-D-thiogalactopyranoside is important in the field of carbohydrate chemistry and enzymology, as it can serve as a model substrate for testing the activity and specificity of glycosidic enzymes. Additionally, it can be used in the synthesis of various carbohydrate-based compounds. Due to its potential applications in both research and industry, ethyl 4,6-O-benzylidene-β-D-thiogalactopyranoside is a valuable chemical in the study of carbohydrate biochemistry.

Upstream product

• 100-52-7 benzaldehyde 
• 56245-60-4 ethyl 1-thio-β-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 104-15-4 toluene-4-sulfonic acid 
• 7473-36-1 ethyl 1-thio-β-D-glucopyranoside 
• 149563-08-6 (2R,4aR,6S,7R,8S,8aR)-6-(ethylthio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl dibenzoate 
• 604-69-3 β-D-glucose pentaacetate 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 83-87-4 D-glucose pentaacetate 
• 492-61-5 β-D-glucose 

Downstream Products

• 116167-60-3 S-ethyl-6-O-(phenylmethyl)-1-thio-β-D-galactopyranoside 
• 153062-22-7 Ethyl 3-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 201056-71-5 ethyl (5R)-4,6-O-benzylidene-1-thio-3-O-pivaloyl-β-D-glucopyranoside 
• 149563-08-6 (2R,4aR,6S,7R,8S,8aR)-6-(ethylthio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl dibenzoate 
• 499126-40-8 ethyl 3-O-allyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 635310-16-6 Methanesulfonic acid (2R,3R,4R,5R,6S)-4,5-bis-benzyloxy-6-ethylsulfanyl-2-methanesulfonyloxymethyl-tetrahydro-pyran-3-yl ester 
• 636560-77-5 2,4-Diazido-5-((2S,3R,4S,5R,6R)-5-azido-6-azidomethyl-3,4-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexanol 
• 197916-04-4 methyl (11S)-11-[[(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoate 
• 107855-14-1 ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside 
• 174172-99-7 ethyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside 
• 1431081-25-2 ethyl 2,3-di-O-benzyl-4,6-O-bis(4-O-benzyl-3,5-di-O-methoxymethylgalloyl)-1-thio-β-D-glucopyranoside 

Relevant articles and documents

Automated access to well-defined ionic oligosaccharides

Ionic polysaccharides are part of many biological events, but lack structural characterisation due to challenging purifications and complex synthesis. Four monosaccharides bearing modifications not found in nature are used for the automated synthesis of a collection of ionic oligosaccharides. Structural analysis reveals how the charge pattern affects glycan conformation.

Synthesis of Glucuronoxylan Hexasaccharides by Preactivation-Based Glycosylations

The synthesis of two glucuronoxylans is described, which both consist of a pentaxylan backbone and a glucuronic acid linked to the 2 position in the fourth xylose residue from the reducing end. The two target molecules differ in the 4 position of the glucuronic acid where one is unsubstituted while the other contains a methyl ether. The pentaxylan backbone is assembled in four glycosylation reactions with phenyl thioglycoside donors. The couplings are performed by preactivation of the donor with in-situ-generated p-nitrobenzenesulfenyl triflate prior to addition of the acceptor. The glucuronic acids are then attached by Koenigs-Knorr glycosylations followed by deprotections. The syntheses employ a total of 8 steps from monosaccharide building blocks and afford the two glucuronoxylans in 12 and 15 % overall yield. The hexasaccharide products are valuable substrates for investigating the activity and specificity of glucuronoxylan-degrading enzymes.

Efficient one-pot per-: O -acetylation-thioglycosidation of native sugars, 4,6- O -arylidenation and one-pot 4,6- O -benzylidenation-acetylation of S -/ O -glycosides catalyzed by Mg(OTf)2

A sequential one-pot per-O-acetylation-S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated product in high yields. Mg(OTf)2 can also mediate sequential one-pot benzylidenation-acetylation of mono and disaccharide based glycosides and thioglycosides in high yield.