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

General Description

Alpha-D-Glucopyranoside, phenyl 1-thio-, tetraacetate is a chemical compound that is a derivative of alpha-D-glucose. It is commonly used in organic synthesis and as a protective group for the hydroxyl groups in glucose. The compound is a white to off-white crystalline powder and is soluble in most organic solvents. It is stable under normal conditions and is primarily used in research and laboratory settings for various chemical reactions and processes. The tetraacetate moiety provides protection to the hydroxyl group, allowing for selective manipulation of the compound in synthetic chemistry. Overall, alpha-D-Glucopyranoside, phenyl 1-thio-, tetraacetate is an important compound in organic chemistry and is widely used as a building block in the synthesis of various bioactive molecules and pharmaceuticals.

Upstream product

• 108-98-5 thiophenol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 14365-16-3 bis-(phenylthio)-dibutylstannane 
• 604-68-2 α-D-glucopyranose peracetylate 
• 930-69-8 sodium thiophenolate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 882-33-7 diphenyldisulfane 
• 83-87-4 D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 2280-44-6 D-Glucose 
• 108-24-7 acetic anhydride 
• 13035-49-9 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl iodide 
• 1417991-40-2 C₂₃H₃₀O₇S 

Downstream Products

• 13992-15-9 phenyl-1-thio-α-D-glucopyranoside 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 107961-09-1 β-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 604-70-6 tetra-O-acetyl-1-O-methyl-β-D-glucopyranose 
• 74808-17-6 methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 107961-09-1 α-1-deoxy-1-C-<(phenylthio)bis(methoxycarbonyl)methyl>-2,3,4,6-tetra-O-acetyl-D-glucopyranose 
• 100432-86-8 1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 65615-62-5 Bromo-acetic acid (5R,6R)-5-acetoxy-6-acetoxymethyl-4-oxo-2-phenylsulfanyl-5,6-dihydro-4H-pyran-3-yl ester 
• 65615-61-4 D-Erythro-Hex-1-enopyranosid-3-ulose 
• 53438-23-6 phenylsulfonyl 2,3,4,6-tetra-O-acetyl-1-deoxy-β-D-glucopyranoside 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 3947-62-4 2,3,4,6-tetraacetylglucose 
• 2936-70-1 phenyl 1-thio-D-glucopyranoside 

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

Rhamnogalacturonan II: Chemical Synthesis of a Substructure Including α-2,3-Linked Kdo**

The synthesis of a fully deprotected Kdo-containing rhamnogalacturonan II pentasaccharide is described. The strategy relies on the preparation of a suitably protected homogalacturonan tetrasaccharide backbone, through a post-glycosylation oxidation approach, and its stereoselective glycosylation with a Kdo fluoride donor.

How do Various Reaction Parameters Influence Anomeric Selectivity in Chemical Glycosylation with Thioglycosides and NIS/TfOH Activation?

The reaction of glycosyl donor phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside with NIS/TfOH(cat.) was systematically studied under various reaction conditions. Neither the molecular sieve pore size nor amount of NIS activator was found to have a