13343-66-3

Basic information

• Product Name: BENZYL 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE
• Synonyms: BENZYL 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE;BENZYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE;Benzyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside;BENZYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-SS-D-GLUCOPYRANOSIDE;b-D-Glucopyranoside, phenylMethyl2-(acetylaMino)-2-deoxy-, 3,4,6-triacetate
• CAS NO: 13343-66-3
• Molecular Formula: C₂₁H₂₇NO₉
• Molecular Weight: 437.44
• Mol File: 13343-66-3.mol

Chemical Properties

• Boiling Point: 586.955 °C at 760 mmHg
• Flash Point: 308.779 °C
• Appearance: /
• Density: 1.267 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.532
• CAS DataBase Reference: BENZYL 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE(13343-66-3)
• EPA Substance Registry System: BENZYL 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE(13343-66-3)

Safety Data

• Hazardous Substances Data: 13343-66-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
BENZYL 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE is used as a synthetic intermediate for the creation of various glycosides and glycoconjugates, which are essential in the development of new pharmaceuticals. Its unique structure allows for the exploration of carbohydrate-based drug candidates, potentially leading to the discovery of novel therapeutic agents.
Used in Carbohydrate Chemistry Research:
In the field of carbohydrate chemistry, BENZYL 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE serves as a model compound for studying the interactions between carbohydrates and other biomolecules. Its acetylated structure provides insights into the effects of different functional groups on the solubility and stability of carbohydrate molecules.
Used in Diagnostic Tool Development:
BENZYL 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE is also utilized in the development of diagnostic tools, where its specific binding properties and reactivity can be harnessed to create assays and tests for detecting the presence of certain biological markers or pathogens.
Used in the Synthesis of Bioactive Compounds:
Due to its versatile structure, BENZYL 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE is employed in the synthesis of bioactive compounds with potential applications in medicine, such as anti-inflammatory, antiviral, or antibacterial agents.
Used in the Food Industry:
Although not explicitly mentioned in the provided materials, given its role in carbohydrate chemistry, BENZYL 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE could potentially be used in the food industry for the development of new sweeteners or flavor enhancers, leveraging its ability to interact with taste receptors.
Each application highlights the versatility and importance of BENZYL 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE in various scientific and industrial fields, emphasizing its potential impact on future discoveries and innovations.

InChI:InChI=1/C21H27NO9/c1-12(23)22-18-20(30-15(4)26)19(29-14(3)25)17(11-27-13(2)24)31-21(18)28-10-16-8-6-5-7-9-16/h5-9,17-21H,10-11H2,1-4H3,(H,22,23)/t17-,18-,19-,20-,21-/m1/s1

Upstream product

• 108-24-7 acetic anhydride 
• 126777-92-2 3,4,6-tetra-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranosyl azide 
• 100-51-6 benzyl alcohol 
• 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 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 2873-29-2 D-glucal triacetate 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 10375-65-2 benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 3055-51-4 benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside 
• 496924-01-7 benzyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranoside 

Downstream Products

• 10375-65-2 benzyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-α-D-glucopyranoside 
• 79184-08-0 3,4,6-tri-O-acetyl-2-acetamido-1-O-[bis(benzyloxy)phophoryl]-2-deoxy-α-D-glucopyranose 
• 147072-52-4 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphanyloxy)-tetrahydro-pyran-4-yl ester 
• 1276112-92-5 benzyl 2-acetamido-2-deoxy-4-O-sulfonato-β-D-galactopyranoside sodium salt 
• 134308-75-1 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 868161-61-9 benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 1287768-44-8 C₃₆H₃₉N₇O₁₅ 
• 1287768-43-7 C₅₅H₅₈N₄O₁₅ 
• 1287768-41-5 C₅₆H₅₆N₄O₁₄ 
• 1287768-18-6 C₅₃H₅₄N₄O₁₄ 
• 1287768-36-8 benzyl 2-acetamido-3-O-propargyloxy-4-O-acetyl-6-O-benzyl-2-deoxy-β-D-galactopyranoside 
• 1287768-35-7 benzyl 2-acetamido-3-O-propargyloxy-4-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 1287768-34-6 benzyl 2-acetamido-3-O-propargyl-6-O-benzyl-2-deoxy-β-D-galactopyranoside 

Relevant articles and documents

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.

Monosaccharide inhibitors targeting carbohydrate esterase family 4 de-N-acetylases

The Carbohydrate Esterase family 4 contains virulence factors which modify peptidoglycan and biofilm-related exopolysaccharides. Despite the importance of this family of enzymes, a potent mechanism-based inhibition strategy has yet to emerge. Based on the postulated tridentate binding mode of the tetrahedral de-N-acetylation intermediate, GlcNAc derivatives bearing metal chelating groups at the 2 and 3 positions were synthesized. These scaffolds include 2-C phosphonate, 2-C sulfonamide, 2-thionoacetamide warheads as well as derivatives bearing thiol, amine and azide substitutions at the 3-position. The inhibitors were assayed against a representative peptidoglycan deacetylase, Pgda from Streptococcus pneumonia, and a representative biofilm-related exopolysaccharide deacetylase, PgaB from Escherichia coli. Of the inhibitors evaluated, the 3-thio derivatives showed weak to moderate inhibition of Pgda. The strongest inhibitor was benzyl 2,3-dideoxy-2-thionoacetamide-3-thio-β-D-glucoside, whose inhibitory potency showed an unexpected dependence on metal concentration and was found to have a partial mixed inhibition mode (Ki = 2.9 ± 0.6 μM).

Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs

Lipo-chitotetrasaccharide analogues where one central GlcNAc residue was replaced by a triazole unit have been synthesized from a derivative obtained by chitin depolymerization and a functionalized N-acetyl-glucosamine via the copper-catalyzed azide-alkyn

Syntheses of N-aryl-protected glucosamines and their stereoselectivity in chemical glycosylations

N-Aryl-protecting groups were introduced in glucosamines to achieve β-selective glycosylation. Various N-aryl aminosugars were synthesized via Buchwald–Hartwig reaction. Glycosylation using glycosyl trichloroacetimidates of N-aryl aminosugars smoothly proceeded in the presence of trimethylsilyl trifluoromethanesulfonate. Use of a glycosyl donor comprising an electron-donating 2,4-dimethoxyphenyl (DMP) group led to the glycosylation proceeding with high β selectivity. This stereoselectivity seemed to be derived from the formation of an aziridine intermediate. The DMP-protecting group can be removed immediately by using ammonium hexanitratocerate (IV).

Ceric ammonium nitrate/acetic anhydride: A tunable system for the O-acetylation and mononitration of diversely protected carbohydrates

Esterification of a wide range of partially protected carbohydrate derivatives was achieved using acetic anhydride and a catalytic amount of ceric ammonium nitrate (CAN). Compatibility with the commonly used protecting groups was demonstrated, with the es

Chemoenzymatic Synthesis of 4-Fluoro-N-Acetylhexosamine Uridine Diphosphate Donors: Chain Terminators in Glycosaminoglycan Synthesis

Unnatural uridine diphosphate (UDP)-sugar donors, UDP-4-deoxy-4-fluoro-N-acetylglucosamine (4FGlcNAc) and UDP-4-deoxy-4-fluoro-N-acetylgalactosamine (4FGalNAc), were prepared using both chemical and chemoenzymatic syntheses relying on N-acetylglucosamine-

Direct glycosylation of unprotected and unactivated sugars using bismuth nitrate pentahydrate

Bi(NO3)3, a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high α-selectivity. Further, an expedient separation of α- and β-glycosides using silver nitrate-impregnated silica gel flash liquid chromatography has been developed.

N-Acetylglucosamine-based efficient, phase-selective organogelators for oil spill remediation

Two simple, eco-friendly and efficient phase-selective gelators were developed for instant (45 s) gelation of oil (either commercial fuels or pure organic liquids) from an oil-water mixture at room temperature to combat marine oil spills.

Order of reactivity of OH/NH groups of glucosamine hydrochloride and N -Acetyl glucosamine toward benzylation using NaH/BnBr in DMF

The order of reactivity of OH and NH groups of glucosamine hydrochloride (GlcNH2HCl) and N-acetyl glucosamine (GlcNAc) toward benzylation with NaH/BnBr in DMF was investigated. For GlcNH2.HCl, benzyl groups were introduced in the order of N-Bn > N-Bn2 > 1-O-Bn > 6-O-Bn > 4-O-Bn > 3-O-Bn; for GlcNAc, benzyl groups were introduced in the order of 1-O-Bn > 6-O-Bn > 4-O-Bn > 3-O-Bn > N-Bn. A range of partially benzylated 2-N,N′-dibenzyl glucopyranosides and GlcNAc derivatives were obtained in a single step. Taylor & Francis Group, LLC.

Synthesis of modified peptidoglycan precursor analogues for the inhibition of glycosyltransferase

The peptidoglycan glycosyltransferases (GTs) are essential enzymes that catalyze the polymerization of glycan chains of the bacterial cell wall from lipid II and thus constitute a validated antibacterial target. Their enzymatic cavity is composed of a donor site for the growing glycan chain (where the inhibitor moenomycin binds) and an acceptor site for lipid II substrate. In order to find lead inhibitors able to fill this large active site, we have synthesized a series of substrate analogues of lipid I and lipid II with variations in the lipid, the pyrophosphate, and the peptide moieties and evaluated their biological effect on the GT activity of E. coli PBP1b and their antibacterial potential. We found several compounds able to inhibit the GT activity in vitro and cause growth defect in Bacillus subtilis. The more active was C16-phosphoglycerate-MurNAc-(l-Ala-d-Glu)-GlcNAc, which also showed antibacterial activity. These molecules are promising leads for the design of new antibacterial GT inhibitors.