93221-21-7

Basic information

• Product Name: 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl isothiocyanate
• Synonyms: 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl isothiocyanate;2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyl isothiocyanate;alpha-D-Mannopyranosyl isothiocyanate 2,3,4,6-tetraacetate
• CAS NO: 93221-21-7
• Molecular Formula: C₁₅H₁₉NO₉S
• Molecular Weight: 389.379
• Product Categories: Carbohydrates
• Mol File: 93221-21-7.mol
• Article Data: 26

Chemical Properties

• Melting Point: 81-82 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 469.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.40±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl isothiocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl isothiocyanate(93221-21-7)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl isothiocyanate(93221-21-7)

Safety Data

• Hazardous Substances Data: 93221-21-7(Hazardous Substances Data)

Usage

General Description

2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl isothiocyanate is a chemical compound that is a derivative of mannose, a type of sugar. It is commonly used in biochemistry and molecular biology as a reagent for the labeling and detection of glycoproteins. The compound is known for its ability to bind to glycoproteins, which are proteins that have sugar molecules attached to them. This property makes it useful for studying and analyzing glycoproteins in various biological processes, including cell signaling, protein function, and disease mechanisms. Additionally, the compound also has potential applications in pharmaceutical research and drug development due to its unique chemical properties.

Upstream product

• 572-09-8 2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide 
• 333-20-0 potassium thioacyanate 
• 14227-52-2 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl chloride 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide 
• 13242-53-0 acetobromomannose 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 83-87-4 penta-O-acetyl-α-D-galactopyranose 
• 572-09-8 acetobromogalactose 
• 25878-60-8 D-galactose pentaacetate 
• 943860-86-4 2-methyl-4,5-dihydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-galactopyrano)[2,1-d]-2-oxazoline 

Downstream Products

• 1174340-48-7 N-[(1R,2R)-2-aminocyclohexyl]-N'-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-thiourea 
• 1174340-47-6 N-[(1S,2S)-2-aminocyclohexyl]-N'-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-thiourea 
• 1314102-49-2 (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-6-(3-((1R,2R)-2-(diphenylphosphino)cyclohexyl)thioureido)-tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1314102-54-9 (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(3-((1S,2S)-2-(diphenylphosphino)cyclohexyl)thioureido)-tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1444827-56-8 5-benzoyl-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole 
• 1444827-58-0 5-p-nitrobenzoyl-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole 
• 1444827-59-1 5-(4-methylbenzoyl)-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole 
• 1444827-60-4 5-(4-cyanobenzoyl)-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole 
• 1444827-64-8 5-(adamantane-1-carbonyl)-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole 
• 1444827-69-3 5-p-nitrobenzoyl-2-((α-D-mannopyranos-1-yl)amino)thiazole 
• 1444827-71-7 5-(4-cyanobenzoyl)-2-((α-D-mannopyranos-1-yl)amino)thiazole 
• 77489-39-5 2,3,4,6-tetra-O-acetyl-1-N--β-D-galactopyranosylamine 
• 108275-74-7 N-(p-bromophenacyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)thiourea 

Relevant articles and documents

Facile control of the self-assembled structures of polylysines having pendent mannose groups via pH and surfactant

A mannose-modified polylysine was synthesized, the self-assembly of which in aqueous solution led to the formation of spherical micelles, vesicles and rod-like micelles in a controlled manner by simply changing the solution pH and adding a surfactant to the solution.

Synthesis of some new carbohydrate-containing thiouriedonaphtho-quinones

Abstract New alkyl, aryl, and glycosylthiouriedo derivatives of 2,3-diamino-1,4-naphthoquinone were synthesized via the reaction of isothiocyanates with 2,3-diamino-1,4-naphthoquinone. The new compounds were fully characterized through their physicochemical properties.

Thiazolylaminomannosides as potent antiadhesives of type 1 piliated escherichia coli isolated from crohn's disease patients

Adherent-invasive Escherichia coli (AIEC) have previously been shown to induce gut inflammation in patients with Crohn's disease (CD). We developed a set of mannosides to prevent AIEC attachment to the gut by blocking the FimH bacterial adhesin. The crystal structure of the FimH lectin domain in complex with a lead thiazolylaminomannoside highlighted the preferential position for pharmacomodulations. A small library of analogues showing nanomolar affinity for FimH was then developed. Notably, AIEC attachment to intestinal cells was efficiently prevented by the most active compound and at around 10000-fold and 100-fold lower concentrations than mannose and the potent FimH inhibitor heptylmannoside, respectively. An ex vivo assay performed on the colonic tissue of a transgenic mouse model of CD confirmed this antiadhesive potential. Given the key role of AIEC in the chronic intestinal inflammation of CD patients, these results suggest a potential antiadhesive treatment with the FimH inhibitors developed.