10294-12-9

Basic information

• Product Name: 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α,β-D-mannopyranose
• Synonyms: 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α,β-D-mannopyranose
• CAS NO: 10294-12-9
• Molecular Weight: 347.322
• Mol File: 10294-12-9.mol
• Article Data: 51

Chemical Properties

• CAS DataBase Reference: 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α,β-D-mannopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α,β-D-mannopyranose(10294-12-9)
• EPA Substance Registry System: 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α,β-D-mannopyranose(10294-12-9)

Safety Data

• Hazardous Substances Data: 10294-12-9(Hazardous Substances Data)

Upstream product

• 65371-97-3 (E/Z)-prop-1-enyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 107-18-6 allyl alcohol 
• 10375-65-2 benzyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-α-D-glucopyranoside 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 63064-48-2 allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 76375-60-5 (3R,4R,5R,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate 
• 90-76-6 2-deoxy-2-amino glucose 
• 108-24-7 acetic anhydride 
• 51533-00-7 2-acetylamino-3,4,6-triacetyl-2-deoxy-α-D-glucopyranosyl bromide 
• 170641-93-7 2-acetamido-1-O-butyroyl-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose 

Downstream Products

• 63064-48-2 allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 658714-97-7 tert-butylphenyl-1H,1H,2H,2H-heptadecafluorodecyloxysilyl 3,4,6-tri-O-acetyl-2-deoxy-2-acetyl-β-D-glucopyranoside 
• 1233921-11-3 p-nitrophenoxycarbonyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside 
• 1338916-88-3 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-cyano-2-(methylthio)-6-phenylpyrimidin-4(1H)-one 
• 1338916-89-4 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-(4-methylphenyl)-2-(methylthio)pyrimidin-4(1H)-one 
• 1338916-90-7 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-(4-methoxyphenyl)-2-(methylthio)pyrimidin-4(1H)-one 
• 1338916-91-8 1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-5-cyano-2-(methylthio)-6-phenylpyrimidin-4(1H)-one 
• 1338916-92-9 1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-(4-methylphenyl)-2-(methylthio)-pyrimidin-4(1H)-one 
• 1338916-93-0 1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-(4-methoxyphenyl)-2-(methylthio)-pyrimidin-4(1H)-one 
• 1338917-06-8 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-phenylpyrimidin-4(1H)-one 
• 1338917-07-9 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-(4-methylphenyl)-pyrimidin-4(1H)-one 
• 1338917-08-0 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-(4-methoxyphenyl)-pyrimidin-4(1H)-one 
• 1338917-09-1 1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-phenyl-pyrimidin-4(1H)-one 
• 1338917-10-4 1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-5-cyano-6-(4-methylphenyl)-pyrimidin-4(1H)-one 

Relevant articles and documents

Development of regioselective deacylation of peracetylated β-d-monosaccharides using lipase from Pseudomonas stutzeri under sustainable conditions

The lipase-catalyzed regioselective deacylation of peracetylated pyranosides has been evaluated in biosolvents. Among the biocatalysts tested, lipase from Pseudomonas stutzeri showed the highest activity, displaying regiospecific activity towards the anomeric position. This lipase was also employed in the regioselective alcoholysis of peracetylated sugars in green solvents, contributing to improve the sustainability of the process. Yields up to 97% of the desired product with different biosolvents were found. These reactions took place without noticeable activity and with total regioselectivity, representing a considerable improvement over the use of an aqueous buffer or conventional organic solvents. Furthermore, scaled up reactions are feasible without losing catalytic action. In order to understand the role of these biosolvents in the enzyme's synthetic behaviour, molecular modelling and docking studies were performed in the presence of some selected biosolvents to conclude that the presence of biosolvents in the reaction media modifies the access of the alcohols to the enzymatic active site allowing the presence of small alcohols and not i-propyl and t-butyl residues in the alcohol. This journal is

NEW METHOD FOR THE 1-DEACETYLATION OF PERACETATES OF AMINOSUGARS

A method for the selective O-deacetylation at the glycosidic centers of aminosugar peracetates is proposed.

Enzymes in Carbohydrate Synthesis: Lipase-Catalyzed Selective Acylation and Deacylation of Furanose and Pyranose Derivatives

A number of furanose and pyranose derivatives were selectively acylated and deacylated on a preparative scale in lipase-catalyzed reactions.The primary hydroxyl functions of the methyl furanosides of D-ribose, D-arabinose, D-xylose, and 2-deoxy-D-ribose were selectively acetylated by crude porcine pancreatic lipase in tetrahydrofuran by using 2,2,2-trifluoroethyl acetate as the acyl donor.Selective deacetylations of the primary hydroxyl functions in the peracetylated methyl furanosides of D-ribose, D-arabinose, D-xylose, and 2-deoxy-D-ribose were best accomplished in a 9:1 solution of 0.1 N phosphate buffer (pH 7) and N,N-dimethylformamide using Candida cylindracea lipase.Selective cleavage of the 1-O-acetyl groups from 1,2,3,5-tetra-O-acetyl-D-ribose and -D-xylose were similarly accomplished with Aspergillus niger lipase.Similar regioselectivites were observed in the pyranose series.The Candida lipase was found to be the best for selective deacylation of the primary position from the peracylated methyl pyranosides, and porcine pancreatic lipase was the best for selective hydrolysis of the 1-O-acetyl groups from peracetylated pyranoses.

Design of a "turn-off/turn-on" biosensor: Understanding carbohydrate-lectin interactions for use in noncovalent drug delivery

A low-cost and highly sensitive biosensor system is designed to investigate carbohydrate-lectin interactions. This combination of glyco-gold nanoparticles and boronic acid biosensor system opens a way to study noncovalent drug delivery.

Galactose Derivative-Modified Nanoparticles for Efficient siRNA Delivery to Hepatocellular Carcinoma

Successful siRNA therapy requires suitable delivery systems with targeting moieties such as small molecules, peptides, antibodies, or aptamers. Galactose (Gal) residues recognized by the asialoglycoprotein receptor (ASGPR) can serve as potent targeting moieties for hepatocellular carcinoma (HCC) cells. However, efficient targeting to HCC via galactose moieties rather than normal liver tissues in HCC patients remains a challenge. To achieve more efficient siRNA delivery in HCC, we synthesized various galactoside derivatives and investigated the siRNA delivery capability of nanoparticles modified with those galactoside derivatives. In this study, we assembled lipid/calcium/phosphate nanoparticles (LCP NPs) conjugated with eight types of galactoside derivatives and demonstrated that phenyl β-d-galactoside-decorated LCP NPs (L4-LCP NPs) exhibited a superior siRNA delivery into HCC cells compared to normal hepatocytes. VEGF siRNAs delivered by L4-LCP NPs downregulated VEGF expression in HCC in vitro and in vivo and led to a potent antiangiogenic effect in the tumor microenvironment of a murine orthotopic HCC model. The efficient delivery of VEGF siRNA by L4-LCP NPs that resulted in significant tumor regression indicates that phenyl galactoside could be a promising HCC-targeting ligand for therapeutic siRNA delivery to treat liver cancer.

Syntheses of α-Linked Derivatives of N-Acetyl Glucosamine and Gal-β(1-3)GalNAc (T Antigen) directly with the Natural N-Acetyl Protecting Group

α-Linked spacer arms, suitable for coupling on a protein carrier, have been introduced directly on GlcNAc and on Gal-β(1-3)GalNAc in a 1,2-cis fashion through a new procedure involving a completely stereoselective Michael addition of the anomeric sodium alcoholate onto β-tosyloxy acrolein prepared in situ from the sodium salt of malonaldehyde and tosyl chloride.

Synthesis and Biological Activity of 3,4,-Tri-О-Acetyl-N-Acetylglucosamine and Tetraacetylglucopyranose Conjugated with Alkyl Phosphates

Abstract: Conjugates of 3,4,6-tri-О-acetyl-N-acetylglucosamine and tetraacetyl glucopyranose with alkyl phosphates were synthesized. The dependence of their antibacterial and antituberculosis activities on the length of the alkyl substituent at the phosphate group was found. The conjugates with a decyl substituent exhibited in vitro the highest antituberculosis activity against Mycobacterium tuberculosis H37Rv (MIC 3?μg/mL) but the weakest effect towards Streptococcus aureus and Bacillus cereus (≤MIC 125 μg/mL). Vice versa, the conjugates with a cetyl substituent demonstrated the highest antibacterial activity in vitro towards S. aureus and B. cereus (MIC 16 μg/mL) but showed the lowest antituberculosis activity (MIC 12 μg/mL) among the compounds under study.

Hafnium(IV) triflate as a potent catalyst for selective 1-O-deacetylation of peracetylated saccharides

An efficient method for selective anomeric deacetylation of peracetylated mono-, di-, and trisaccharides has been developed by using 2 mol% Hf(OTf)4 as catalyst in acetonitrile. Employment of ultrasonic irradiation could significantly accelerate the reaction rate. Mechanistic study confirmed the hydrolysis nature of this reaction, and NMR experimental data suggested that multiple peracetylated saccharide molecules may ligate to Hf(IV) cation primarily via the anomeric acetate to promote its specific hydrolysis.

The effect of deoxyfluorination and: O -acylation on the cytotoxicity of N -acetyl-d-gluco- And d-galactosamine hemiacetals

Fully acetylated deoxyfluorinated hexosamine analogues and non-fluorinated 3,4,6-tri-O-acylated N-acetyl-hexosamine hemiacetals have previously been shown to display moderate anti-proliferative activity. We prepared a set of deoxyfluorinated GlcNAc and GalNAc hemiacetals that comprised both features: O-acylation at the non-anomeric positions with an acetyl, propionyl and butanoyl group, and deoxyfluorination at selected positions. Determination of the in vitro cytotoxicity towards the MDA-MB-231 breast cancer and HEK-293 cell lines showed that deoxyfluorination enhanced cytotoxicity in most analogues. Increasing the ester alkyl chain length had a variable effect on the cytotoxicity of fluoro analogues, which contrasted with non-fluorinated hemiacetals where butanoyl derivatives had always higher cytotoxicity than acetates. Reaction with 2-phenylethanethiol indicated that the recently described S-glyco-modification is an unlikely cause of cytotoxicity.

Generation of a glycosylated asparagine residue through chemoselective acylation of a glycosylhydrazide

Herein, we report the first selective anomeric N-acylation of a glycosylhydrazide. We show that this transformation can be harnessed to generate amino acid building blocks including FmocAsn(GlcNAc)OH (1), a residue that has been previously shown to be a c