35785-42-3

Usage

Uses

Used in Organic Synthesis:
4-Nitrobenzyl 2,3,4,6-Tetra-O-acetyl-1-thio--D-galactopryranoside is used as a key intermediate in the synthesis of 1-thio-β-D-glycopyranosides. These glycosides are important building blocks in the preparation of various biologically active compounds, including pharmaceuticals, agrochemicals, and other bioactive molecules. 4-Nitrobenzyl 2,3,4,6-Tetra-O-acetyl-1-thio--D-galactopryranoside's unique structure allows for selective reactions and modifications, making it a valuable tool in the synthesis of complex carbohydrate derivatives.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Nitrobenzyl 2,3,4,6-Tetra-O-acetyl-1-thio--D-galactopryranoside is used as a precursor for the development of novel therapeutic agents. 4-Nitrobenzyl 2,3,4,6-Tetra-O-acetyl-1-thio--D-galactopryranoside's ability to form glycosidic linkages with other molecules makes it a promising candidate for the creation of new drugs with improved pharmacological properties, such as enhanced solubility, stability, and bioavailability.
Used in Carbohydrate Chemistry Research:
4-Nitrobenzyl 2,3,4,6-Tetra-O-acetyl-1-thio--D-galactopryranoside is also used in academic and research settings to study the chemistry of carbohydrates and their interactions with other biomolecules. Researchers use 4-Nitrobenzyl 2,3,4,6-Tetra-O-acetyl-1-thio--D-galactopryranoside to investigate the mechanisms of glycosylation, enzyme inhibition, and other carbohydrate-related processes, which can lead to a better understanding of carbohydrate biology and the development of new therapeutic strategies.

Upstream product

• 19879-84-6 O²,O³,O⁴,O⁶-Tetraacetyl-1-thio-D-glucose 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 19879-84-6 tetraacetyl thioglucose 
• 604-69-3 β-D-glucose pentaacetate 
• 19879-84-6 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 13242-53-0 acetobromomannose 
• 25878-60-8 D-galactose pentaacetate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 19879-84-6 2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose 
• 84062-53-3 2,3,4,6-tetra-O-acetylgalactopyranosyl-1-β-pseudothiourea hydrobromide 
• 4163-60-4 β-D-galactose peracetate 
• 39549-05-8 bis(4-nitrobenzyl)disulfide 
• 100-14-1 4-nitrobenzyl chloride 
• 40591-65-9 2,3,4,6-tetra-O-acetylgalactopyranosyl-1-β-pseudothiourea hydrobromide 

Downstream Products

• 161761-58-6 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-{4-[6-(2,2,2-trifluoro-acetylamino)-hexanoylamino]-benzylsulfanyl}-tetrahydro-pyran-4-yl ester 
• 161761-60-0 6-[6-(2,2,2-Trifluoro-acetylamino)-hexanoylamino]-hexanoic acid [4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanylmethyl)-phenyl]-amide 
• 161761-61-1 1-deoxy-1-benzythio>-β-D-glucopyranose 
• 161761-59-7 1-deoxy-1--β-D-glucopyranose 

Relevant academic research and scientific papers

Development of photoswitchable inhibitors for β-galactosidase

Azobenzenes are of particular interest as a photochromic scaffold for biological applications because of their high fatigue resistance, their large geometrical change between extended (trans) and bent (cis) isomer, and their diverse synthetic accessibility. Despite their wide-spread use, there is no reported photochromic inhibitor of the well-investigated enzyme β-galactosidase, which plays an important role for biochemistry and single molecule studies. Herein, we report the synthesis of photochromic competitive β-galactosidase inhibitors based on the molecular structure of 2-phenylethyl β-d-thiogalactoside (PETG) and 1-amino-1-deoxy-β-d-galactose (β-d-galactosylamine). The thermally highly stable PETG-based azobenzenes show excellent photochromic properties in polar solvents and moderate to high photostationary states (PSS). The optimized compound 37 is a strong competitive inhibitior of β-galactosidase from Escherichia coli and its inhibition constant (Ki) changes between 60 nM and 290 nM upon irradiation with light. Additional docking experiments supported the observed structure-activity relationship.

Synthesis of thio- and selenoglycosides by cleavage of dichalconides in the presence of zinc/zinc chloride and reaction with glycosyl bromides

A convenient odorless methodology has been devised for the preparation of 1,2-trans-thio- and selenoglycosides through zinc-mediated cleavage of disulfides and diselenides and reaction of the thiolate and selenides formed in situ with glycosyl bromides. T

Modified one-pot protocol for the preparation of thioglycosides from unprotected aldoses via S-glycosyl isothiouronium salts

An efficient one-pot protocol for the direct preparation of thioglycosides starting from unprotected reducing sugars via S-glycosyl isothiouronium salts is reported. In this one-pot methodology, BF3·OEt2 has been used as a general catalyst for both per-O-acetylation of sugars and conversion of sugar per-O-acetates into S-glycosyl isothiouronium salts, which was allowed to react with alkylating agents in the presence of a base to furnish thioglycosides in excellent yield. Copyright Taylor & Francis, Inc.

Reaction of 1,2-trans-glycosyl acetates with thiourea: A new entry to 1-thiosugars

The reaction of 1,2-trans-glycosyl acetates with thiourea under boron trifluoride etherate catalysis affording acetylated S-glycosyl isothiourea derivatives is described. The isothiourea derivatives obtained can be readily transformed into the desired 1-thiosugar derivative by reaction with triethylamine and subsequent alkylation or acylation of the in situ formed 1-thioaldose.

A general procedure for conversion of S-glycosyl isothiourea derivatives into thioglycosides, thiooligosaccharides and glycosyl thioesters

A simple procedure for conversion of S-glycosyl isothiourea derivatives into thioglycosides by promotion with triethylamine is described. The reaction conditions allow the synthesis of glycosyl thioesters and some thioglycosides, which cannot be prepared using the traditional approach. The procedure has been successfully applied for preparation of thiooligosaccharides, shown by syntheses of methyl 4-thio-α-cellobioside and methyl 4-thio-α-lactoside derivatives.

SYNTHESIS OF A LIGAND BASED ON 1-DEOXY-1-(p-AMINOBENZYLTHIO)-β-D-GLUCOPYRANOSE FOR AFFINITY CHROMATOGRAPHY

A synthesis is reported of 1-deoxy-1-benzylthio>-β-D-glucopyranose, which can be used as a ligand in purification of β-glucosidase by affinity chromatography.The ligand has been obtained by N-acylation of 1-deoxy-1-(p-aminobenzylthio)glucose with 6-(trifluoroacetamido)hexanoic acid, followed by complete deacylation.The corresponding amino derivative was obtained by reduction of 1-deoxy-1-(p-nitrobenzylthio)-β-D-glucopyranose with zinc dust.

INSULIN-LIKE, AND INSULIN-ANTAGONISTIC, CARBOHYDRATE DERIVATIVES. THE SYNTHESIS OF ARYL AND ARALKYL D-MANNOPYRANOSIDES AND 1-THIO-D-MANNOPYRANOSIDES

A number of novel, aryl and aralkyl D-mannopyranosides and 1-thio-D-mannopyranosides were synthesized for evaluation of insulin-like and insulin-antagonistic properties.The substituted-phenyl α-D-mannopyranosides were prepared by the general procedure of Helferich and Schmitz-Hillebrecht, the substituted-phenyl 1-thio-α-D-mannopyranosides by a method corresponding to the Michael synthesis of aromatic glycosides, and the aralkyl 1-thio-α-D-mannopyranosides by aralkylation of 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranose 15 and subsequent O-deacetylation.Compound (15) was obtained by basic cleavage of the amidino group in 2-S-(tetra)-O-acetyl-α-D-mannopyranosyl)-2-thiopseudourea hydrobromide, the product of the reaction of tetra-O-acetyl-α-D-mannosyl bromide with thiourea.Benzyl 1-thio-β-D-mannopyranoside, obtained by reaction of the sodium salt of 1-thio-β-D-mannopyranose with α-bromotoluene, and benzyl 1-thio-α-L-mannopyranoside were also synthesized, in order to asses the stereospecificity of the biological activites measured.