4239-72-9

Basic information

• Product Name: Ethyl 3,4,6-Tri-O-acetyl-2-acetamido-2-deoxy-β-D-thioglucopyranoside
• Synonyms: Ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-thioglucopyranoside;Ethyl 2-(AcetylaMino)-2-deoxy-1-thio-β-D-glucopyranoside 3,4,6-Triacetate
• CAS NO: 4239-72-9
• Molecular Formula: C₁₆H₂₅NO₈S
• Molecular Weight: 391.4366
• Product Categories: Amines;Carbohydrates & Derivatives;Sulfur & Selenium Compounds
• Mol File: 4239-72-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 175-177°C
• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Heated, Son
• CAS DataBase Reference: Ethyl 3,4,6-Tri-O-acetyl-2-acetamido-2-deoxy-β-D-thioglucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 3,4,6-Tri-O-acetyl-2-acetamido-2-deoxy-β-D-thioglucopyranoside(4239-72-9)
• EPA Substance Registry System: Ethyl 3,4,6-Tri-O-acetyl-2-acetamido-2-deoxy-β-D-thioglucopyranoside(4239-72-9)

Safety Data

• Hazardous Substances Data: 4239-72-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid, stench

Uses

A reagent for the preparation of GlcNAc glycosides.

Upstream product

• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 
• 3945-29-7 ethyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-1-thio-β-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 75-08-1 ethanethiol 
• 90-76-6 D-galactosamine 
• 5573-62-6 (ethylthio)trimethylsilane 
• 76375-60-5 (3R,4R,5R,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate 
• 187879-61-4 ethyl thioglycoside 
• 165524-87-8 4-O-acetyl-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol 
• 51224-18-1 S-thiouronium 2-N-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside hydrochloride 
• 75-03-6 ethyl iodide 
• 312967-20-7 ethyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 6838-16-0 2-acetamido-2-deoxy-D-glucose diethyl dithioacetal 

Downstream Products

• 312967-20-7 ethyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside 
• 122331-70-8 Ethyl 1-sulfanyl-(2-acetamido-2-deoxy)-O-β-D-glucopyranoside 
• 4229-38-3 2-acetamido-2-deoxy-β-D-glucopyranosylamine 
• 7512-17-6 N-Acetyl-D-glucosamine 

Relevant articles and documents

Chemoenzymatic Synthesis of Glycoconjugates Mediated by Regioselective Enzymatic Hydrolysis of Acetylated 2-Amino Pyranose Derivatives

Highly regioselective deprotection of a series of 2-amino pyranose building blocks was achieved by enzymatic hydrolysis. These monodeprotected intermediates were successfully used in the synthesis of a variety of glycoconjugate derivatives with a core of glucosamine or galactosamine, including neo-glycoproteins and glycosphingolipids. The hydrolysis catalyzed by acetylxylan esterase from Bacillus pumilus (AXE) is suitable for the synthesis of neo-glycoproteins with an N-acetyl glucosamine core. The hydrolysis catalyzed by Candida rugosa lipase (CRL) was successfully applied in the preparation of new sialylated glycolipids starting from glucosamine building blocks protected as phthalimide. This chemoenzymatic approach can be used for the preparation of new glycoconjugate products with anticancer activity.

From glycals to glycopeptides: A convergent and stereoselective total synthesis of a high mannose N-linked glycopeptide

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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.