14086-90-9

Basic information

• Product Name: 2-Acetamido-2-deoxy-1,3,4,6-tetra-0-acetyl-alpha-D-glucopyranose
• Synonyms: D-GLUCOSAMINE PENTAACETATE;2-Acetamido-2-deoxy-1,3,4,6-tetra-0-acetyl-alpha-D-glucopyranose;2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-alpha-D-glucopyranose;1,3,4,6-Tetra-O-acetyl-2-(acetylamino)-2-deoxy-D-glucopyranose, D-Glucosamine pentaacetate, 1,3,4,6-Tetra-O-acetyl-GlcNAc, GlcNAc tetraacetate;2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucopyranose min. 99%;β-D-GlcNAc tetraacetate;beta-D-GlcNAc tetraacetate
• CAS NO: 14086-90-9
• Molecular Formula: C₁₆H₂₃NO₁₀
• Molecular Weight: 389.35
• EINECS: 232-071-0
• Mol File: 14086-90-9.mol
• Article Data: 121

Chemical Properties

• Boiling Point: 530.2 °C at 760 mmHg
• Flash Point: 274.4 °C
• Appearance: /
• Density: 1.3 g/cm³
• Storage Temp.: -20°C
• PKA: 13.41±0.70(Predicted)
• CAS DataBase Reference: 2-Acetamido-2-deoxy-1,3,4,6-tetra-0-acetyl-alpha-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Acetamido-2-deoxy-1,3,4,6-tetra-0-acetyl-alpha-D-glucopyranose(14086-90-9)
• EPA Substance Registry System: 2-Acetamido-2-deoxy-1,3,4,6-tetra-0-acetyl-alpha-D-glucopyranose(14086-90-9)

Safety Data

• Hazardous Substances Data: 14086-90-9(Hazardous Substances Data)

Usage

General Description

2-Acetamido-2-deoxy-1,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose is a complex chemical compound with the molecular formula C14H19NO8. It is a derivative of glucose, and its structure is made up of four acetate groups attached to the hydroxyl groups on the glucose molecule. 2-Acetamido-2-deoxy-1,3,4,6-tetra-0-acetyl-alpha-D-glucopyranose is commonly used in biochemistry and organic chemistry research as a building block for the synthesis of various carbohydrates and glycosides. It also has potential applications in the development of pharmaceuticals and drug delivery systems due to its structural similarity to natural sugars.

Upstream product

• 108-24-7 acetic anhydride 
• 113532-33-5 2-amino-2-deoxy-D-idose; hydrochloride 
• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 
• 66-84-2 D-(+)-glucosamine hydrochloride 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 81336-82-5 2-(trimethylsilyl)ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 64-19-7 acetic acid 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 
• 10036-64-3 N-acetyl-D-glucosamine 
• 7512-17-6 2-acetamido-2-deoxy-D-glucose 
• 75-36-5 acetyl chloride 
• 10387-40-3 potassium thioacetate 

Downstream Products

• 3946-01-8 methyl N-acetyl-β-D-glucosaminide 
• 6082-04-8 methyl 2-acetylamido-2-deoxy-D-glucoside 
• 121356-12-5 [1]naphthyl-(tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranoside) 
• 111443-19-7 2-acetylamino-1,1-diphenyl-1,2-dideoxy-D-glucitol 
• 6195-86-4 methyl 2-acetamido-2-deoxy-3,4,6-tri-O-methyl-β-D-glucopyranoside 
• 131531-80-1 1-(2-naphthyl) 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside 
• 13089-21-9 1-O-phenyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranose 
• 13089-19-5 1-O-phenyl-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose 
• 13089-27-5 p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-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 
• 7512-17-6 2-acetamido-2-deoxy-D-glucose 
• 4239-72-9 ethyl 2-acetamido-3,4,6-tetra-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 50991-93-0 methyl 2-amino-2-deoxy-α-D-mannopyranoside 

Relevant articles and documents

Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents

In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.

S-ANTIGEN TRANSPORT INHIBITING OLIGONUCLEOTIDE POLYMERS AND METHODS

Various embodiments provide STOPS? polymers that are S-antigen transport inhibiting oligonucleotide polymers, processes for making them and methods of using them to treat diseases and conditions. In some embodiments the STOPS? modified oligonucleotides include an at least partially phosphorothioated sequence of alternating A and C units having modifications as described herein. The sequence independent antiviral activity against hepatitis B of embodiments of STOPS? modified oligonucleotides, as determined by HBsAg Secretion Assay, is an EC50 that is less than 100 nM.

A silyl ether-protected building block forO-GlcNAcylated peptide synthesis to enable one-pot acidic deprotection

In this report, we introduce a novel building block for Fmoc/tBu solid phase peptide synthesis (SPPS) of β-linkedO-GlcNAcylated peptides. This building block carries acid labile silyl ether protecting groups, which are fully removed under TFA-mediated peptide cleavage conditions from the resin, thus requiring fewer synthetic steps and no intermediate purification as compared to other acid or base labile protecting group strategies.