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
• Article Data: 35

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

General Description

Benzyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranoside is a complex chemical compound with a molecular structure that includes a benzene ring, an acetamido group, and multiple acetyl groups attached to a glucose molecule. BENZYL 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE is often used in research and pharmaceutical settings as a building block for the synthesis of various glycosides and glycoconjugates. Its unique structure and properties make it useful for studying and modifying carbohydrate molecules, as well as developing potential therapeutic agents and diagnostic tools. Additionally, its acetyl groups and other moieties can influence its solubility, stability, and biological activity, making it an important tool for understanding the role of carbohydrates in biological processes.

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

• 100-51-6 benzyl alcohol 
• 51533-00-7 2-acetylamino-3,4,6-triacetyl-2-deoxy-α-D-glucopyranosyl bromide 
• 439-02-1 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl fluoride 
• 134160-64-8 4',5'-epoxypentyl 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 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 10294-12-9 2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 
• 2873-29-2 D-glucal triacetate 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 108-24-7 acetic anhydride 
• 100-39-0 benzyl bromide 
• 738518-26-8 C₁₃H₁₉NO₅ 

Downstream Products

• 62098-31-1 benzyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-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 
• 10375-65-2 benzyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-α-D-glucopyranoside 
• 1287768-23-3 benzyl 2-acetamido-3,6-di-O-benzyl-4-O-propargyl-2-deoxy-β-D-glucopyranoside 
• 1287768-32-4 benzyl 2-acetamido-3-O-propargyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 1287768-33-5 benzyl 2-acetamido-3-O-propargyl-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 
• 1287768-35-7 benzyl 2-acetamido-3-O-propargyloxy-4-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 1287768-36-8 benzyl 2-acetamido-3-O-propargyloxy-4-O-acetyl-6-O-benzyl-2-deoxy-β-D-galactopyranoside 
• 1287768-18-6 C₅₃H₅₄N₄O₁₄ 
• 1287768-41-5 C₅₆H₅₆N₄O₁₄ 
• 1287768-43-7 C₅₅H₅₈N₄O₁₅ 
• 1287768-44-8 C₃₆H₃₉N₇O₁₅ 

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.

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).

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-