4239-72-9

Upstream product

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

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 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 4229-38-3 2-acetamido-2-deoxy-β-D-glucopyranosylamine 

Relevant academic research and scientific papers

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.

Microwave irradiation for accelerating the synthesis of thioglycosides

A simple and efficient procedure for the synthesis of thioglycosides has been achieved from the reaction of glycosylisothiouronium salts with alkyl or heteroaryl halides under microwave irradiation, in much shorter times and in yields comparable with conventional methods. Copyright Taylor & Francis Group, LLC.

The mild cleavage of 2-amino-2-deoxy-D-glucoside methoxycarbonyl derivatives.

The conversion of methyl carbamate to the corresponding free amine is described for a series of 2-amino-2-deoxy-D-glucosamine derivatives. Cleavage of methoxycarbonyl moiety with MeSiCl(3) and triethylamine in dry THF at 60 degrees C and subsequent aqueou

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

Synthesis of Ethyl and Phenyl 1-Thio-1,2-trans-D-Glycopyranosides from the Corresponding Per-O-Acetylated Glycopyranoses having a 1,2-trans-Configuration using Anhydrous Ferric Chloride as a Promoter

The reaction between per-O-acetylated hexopyranoses and suitable thiols in the presence of anhydrous ferric chloride affords the corresponding thioglycosides.Thus, ethyl 1-thio-β-D-glycopyranosides were prepared as per-O-acetates in gluco, 2-acetamido-2-deoxy-gluco-, 2-deoxy-phthalimido-gluco-, and 2-chloroacetamido-2-deoxy-gluco-configurations.Ethyl 1-thio-α-D-mannopyranoside was prepared from a suitable per-O-acetate, as was phenyl tetra-O-acetyl-1-thio-β-D-glucopyranoside, using thiophenol as the glycosylating agent.Prolonged reaction time adversely affects the yield.A reaction scheme is proposed that explains this observation.