13992-16-0

Basic information

• Product Name: .alpha.-D-Glucopyranoside, phenyl 1-thio-, tetraacetate
• Synonyms: .alpha.-D-Glucopyranoside, phenyl 1-thio-, tetraacetate;phenyl 2,3,4,6-tetra-O-acetyl-α-D-1-thio-Mannoside;Phenyl 2,3,4,6-tetra-O-acetyl-α-D-thiomannopyranoside;Phenyl 1-thio-alpha-D-glucopyranoside 2,3,4,6-tetraacetate
• CAS NO: 13992-16-0
• Molecular Formula: C₂₀H₂₄O₉S
• Molecular Weight: 440.46
• Mol File: 13992-16-0.mol
• Article Data: 179

Chemical Properties

• Melting Point: 85-87°C
• Boiling Point: 514.6±50.0 °C(Predicted)
• Appearance: /
• Density: 1.31±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: .alpha.-D-Glucopyranoside, phenyl 1-thio-, tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: .alpha.-D-Glucopyranoside, phenyl 1-thio-, tetraacetate(13992-16-0)
• EPA Substance Registry System: .alpha.-D-Glucopyranoside, phenyl 1-thio-, tetraacetate(13992-16-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 13992-16-0(Hazardous Substances Data)

Usage

Description

.alpha.-D-Glucopyranoside, phenyl 1-thio-, tetraacetate is a chemical compound derived from alpha-D-glucose, characterized by its protective tetraacetate group and a phenyl 1-thio moiety. This white to off-white crystalline powder is soluble in most organic solvents and is stable under normal conditions. It serves as a crucial building block in organic synthesis and is extensively utilized in research and laboratory settings for the synthesis of various bioactive molecules and pharmaceuticals.

Uses

Used in Organic Synthesis:
.alpha.-D-Glucopyranoside, phenyl 1-thio-, tetraacetate is used as a synthetic intermediate for the preparation of complex organic molecules. Its tetraacetate group provides protection to the hydroxyl group, enabling selective manipulation in synthetic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, .alpha.-D-Glucopyranoside, phenyl 1-thio-, tetraacetate is used as a key component in the development of novel drugs. Its unique structure allows for the creation of bioactive molecules with potential therapeutic applications.
Used in Research and Laboratory Settings:
.alpha.-D-Glucopyranoside, phenyl 1-thio-, tetraacetate is utilized as a research tool in various chemical reactions and processes, aiding scientists in understanding the properties and behavior of glucose derivatives and their potential applications in different fields.

Upstream product

• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 108-98-5 thiophenol 
• 882-33-7 diphenyldisulfane 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 
• 604-69-3 β-D-glucose pentaacetate 
• 4163-60-4 β-D-galactose peracetate 
• 2872-65-3 4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 4551-15-9 phenylthiotrimethylsilane 
• 83-87-4 penta-O-acetyl-α-D-galactopyranose 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 74638-65-6 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl iodide 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 6806-56-0 2,3,4,6-tetra-O-acetyl-1S-acetyl-1-thio-β-D-galactopyranose 
• 19879-84-6 2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose 

Downstream Products

• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 53438-23-6 phenylsulfonyl 2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-glucopyranoside 
• 171283-83-3 2-(trimethylsilyl)ethyl 2-zido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranoside 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 439-03-2 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl fluoride 
• 2823-44-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl fluoride 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 3947-62-4 2,3,4,6-tetraacetylglucose 
• 211423-01-7 p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 55676-46-5 2,3,4,6-tetra-O-acetyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-β-D-glucopyranoside 
• 5239-08-7 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-O-diisopropylidene-α-D-galactopyranose 
• 4860-78-0 6-O-acetyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 794591-52-9 1-O-benzoyl-2,4-O-benzylidene-5,6-O-isopropylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-glucitol 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 

Relevant articles and documents

Stereoselective O-Glycosylations by Pyrylium Salt Organocatalysis**

Despite many years of invention, the field of carbohydrate chemistry remains rather inaccessible to non-specialists, which limits the scientific impact and reach of the discoveries made in the field. Aiming to increase the availability of stereoselective

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Total Synthesis of a Partial Structure from Arabinogalactan and Its Application for Allergy Prevention

Arabinogalactan, a microheterogeneous polysaccharide occurring in plants, is known for its allergy-protective activity, which could potentially be used for preventive allergy treatment. New treatment options are highly desirable, especially in a preventive manner, due to the constant rise of atopic diseases worldwide. The structural origin of the allergy-protective activity of arabinogalactan is, however, still unclear and isolation of the polysaccharide is not feasible for pharmaceutical applications due to a variation of the activity of the natural product and contaminations with endotoxins. Therefore, a pentasaccharide partial structure was selected for total synthesis and subsequently coupled to a carrier protein to form a neoglycoconjugate. The allergy-protective activity of arabinogalactan could be reproduced with the partial structure in subsequent in vivo experiments. This is the first example of a successful simplification of arabinogalactan with a single partial structure while retaining its allergy-preventive potential.