122331-70-8

Basic information

• Product Name: Ethyl 2-Acetamido-2-deoxy-β-D-thioglucopyranoside
• Synonyms: Ethyl 2-Acetamido-2-deoxy-β-D-thioglucopyranoside;Ethyl 2-AcetaMido-2-deoxy-
• CAS NO: 122331-70-8
• Molecular Formula: C₁₀H₁₉NO₅S
• Molecular Weight: 265.32656
• Product Categories: Amines;Carbohydrates & Derivatives;Sulfur & Selenium Compounds;Amines, Carbohydrates & Derivatives, Sulfur & Selenium Compounds
• Mol File: 122331-70-8.mol

Chemical Properties

• Melting Point: 216-218°C
• Boiling Point: 566.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.35±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: DMSO, Methanol, Water
• PKA: 13.03±0.70(Predicted)
• CAS DataBase Reference: Ethyl 2-Acetamido-2-deoxy-β-D-thioglucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-Acetamido-2-deoxy-β-D-thioglucopyranoside(122331-70-8)
• EPA Substance Registry System: Ethyl 2-Acetamido-2-deoxy-β-D-thioglucopyranoside(122331-70-8)

Safety Data

• Hazardous Substances Data: 122331-70-8(Hazardous Substances Data)

Usage

Uses

Used in Carbohydrate Chemistry:
Ethyl 2-Acetamido-2-deoxy-β-D-thioglucopyranoside is used as a synthetic intermediate for the preparation of modified carbohydrates with glycosidases. Its application is crucial for the stereoand regiospecific syntheses of lactosamine derivatives and related compounds, which are essential in various biological and pharmaceutical applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Ethyl 2-Acetamido-2-deoxy-β-D-thioglucopyranoside is used as a key component in the development of novel drug candidates. Its ability to facilitate the synthesis of modified carbohydrates with specific stereochemistry and regioselectivity makes it a valuable tool for creating new therapeutic agents targeting various diseases and conditions.
Used in Research and Development:
Ethyl 2-Acetamido-2-deoxy-β-D-thioglucopyranoside is also used in research and development settings, where it serves as a vital compound for exploring the structure, function, and interactions of carbohydrates in biological systems. Its role in the synthesis of lactosamine derivatives and related compounds contributes to a deeper understanding of carbohydrate biology and the development of new diagnostic and therapeutic strategies.

Upstream product

• 4239-72-9 ethyl 2-acetamido-3,4,6-tetra-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 7512-17-6 2-acetamido-2-deoxy-D-glucose 
• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 

Downstream Products

• 263243-35-2 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-5-acetylamino-6-ethylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester 

Relevant articles and documents

Chemoenzymatic synthesis of ethyl 1-thio-(β-D-galactopyranosyl)-O-β-D-glycopyranosyl disaccharides using the β-galactosidase from Bacillus circulans

Different ethyl 1-thio-β-D-disaccharides have been synthesised by transgalactosylation using the β-galactosidase from Bacillus circulans as biocatalyst. This β-galactosidase shows mainly a β-1-4 specificity in the galactosyl transfer. Gal-β-(1-4)-O-β-D-GlcSEt 15 was obtained in 36% yield, Gal-β-(1-4)-O-α-D-GlcSEt 19 in 30% yield, Gal-β-(1-4)-O-β-D-GalSEt 17 in 60% yield, Gal-β-(1-4)-O-β-D-GalNAcSEt 20 in 49% yield, Gal-β-(1-4)-O-β-D-Gal-β-(1-4)-O-β-D-GalNAcSEt 21 in 9% yield, Gal-β-(1-6)-O-β-D-GlcSEt 16 in 3% yield and Gal-β-(1-3)-O-β-D-XylSEt 18 in 25% yield.

Facile Preparation of Glycosyl Donors for Oligosaccharide Synthesis: 2-Azido-2-deoxyhexopyranosyl Building Blocks

Facile routes to the 2-azido-2-deoxy-1-thioglycosides 6, 7, 15, and 18 and of the 2-azido-2-deoxy-4-pentenoglycoside 11, are described.These are useful intermediates for the synthesis of oligo-saccharides containing α-D-2-amino-2-deoxy (or 2-acetamido-2-d