6730-10-5

Basic information

• Product Name: 1,3,4,6-Tetra-O-acetyl-2-(acetylamino)-2-deoxyhexopyranose
• Synonyms: Mannopyranose,2-acetamido-2-deoxy-, 1,3,4,6-tetraacetate, β-D- (8CI);1,3,4,6-Tetra-O-acetyl-2-acetamido-2-deoxy-β-D-mannopyranose;NSC 232059
• CAS NO: 6730-10-5
• Molecular Formula: C₁₆H₂₃NO₁₀
• Molecular Weight: 389.359
• Mol File: 6730-10-5.mol
• Article Data: 121

Chemical Properties

• Boiling Point: 530.2 °C at 760 mmHg
• Flash Point: 274.4 °C
• Density: 1.3 g/cm³
• CAS DataBase Reference: 1,3,4,6-Tetra-O-acetyl-2-(acetylamino)-2-deoxyhexopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4,6-Tetra-O-acetyl-2-(acetylamino)-2-deoxyhexopyranose(6730-10-5)
• EPA Substance Registry System: 1,3,4,6-Tetra-O-acetyl-2-(acetylamino)-2-deoxyhexopyranose(6730-10-5)

Safety Data

• Hazardous Substances Data: 6730-10-5(Hazardous Substances Data)

Usage

General Description

1,3,4,6-Tetra-O-acetyl-2-(acetylamino)-2-deoxyhexopyranose is a chemical compound that belongs to the family of carbohydrates. It is a derivative of 2-deoxyhexose and is commonly used in organic chemistry research and as a building block for the synthesis of various bioactive compounds. 1,3,4,6-Tetra-O-acetyl-2-(acetylamino)-2-deoxyhexopyranose is often utilized as a precursor in the synthesis of complex glycosides and glycoconjugates due to its ability to undergo selective chemical transformations at different positions on the molecule. The acetyl groups on the molecule help to control the reactivity and selectivity of the compound, making it a valuable tool for chemists in the construction of complex carbohydrate molecules. Overall, 1,3,4,6-Tetra-O-acetyl-2-(acetylamino)-2-deoxyhexopyranose plays a crucial role in the development of new pharmaceuticals and materials with potential biological and medical applications.

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 
• 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 
• 14257-69-3 glucosamine 
• 67-56-1 methanol 
• 127-09-3 sodium acetate 
• 10034-19-2 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose hydrochloride 
• 7512-17-6 N-Acetyl-D-glucosamine 

Downstream Products

• 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 
• 2771-48-4 methyl 2-acetamido-3,4,6-O-triacetyl-2-deoxy-β-D-glucopyranoside 
• 72333-20-1 allyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 160168-40-1 N^α-fluoren-9-ylmethoxycarbonyl-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-L-threonine 
• 160067-63-0 N^α-(9-flourenylmethoxycarbonyl)-3-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-Β-D-glucopyranosyl)-L-serine 
• 27526-42-7 phenyl 2-acetamido-3,4,6-tri-O-acetyl-1,2-di-deoxy-1-thio-β-D-glucopyranoside 
• 63064-48-2 allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 10375-65-2 benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 155197-37-8 n-butyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-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 
• 172688-21-0 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-(2-trimethylsilanyl-acetylamino)-tetrahydro-pyran-4-yl ester 

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.

Synthesis of Asparagine Derivatives Harboring a Lewis X Type DC-SIGN Ligand and Evaluation of their Impact on Immunomodulation in Multiple Sclerosis

The protein myelin oligodendrocyte glycoprotein (MOG) is a key component of myelin and an autoantigen in the disease multiple sclerosis (MS). Post-translational N-glycosylation of Asn31 of MOG seems to play a key role in modulating the immune response towards myelin. This is mediated by the interaction of Lewis-type glycan structures in the N-glycan of MOG with the DC-SIGN receptor on dendritic cells (DCs). Here, we report the synthesis of an unnatural Lewis X (LeX)-containing Fmoc-SPPS-compatible asparagine building block (SPPS=solid-phase peptide synthesis), as well as asparagine building blocks containing two LeX-derived oligosaccharides: LacNAc and Fucα1-3GlcNAc. These building blocks were used for the glycosylation of the immunodominant portion of MOG (MOG31-55) and analyzed with respect to their ability to bind to DC-SIGN in different biological setups, as well as their ability to inhibit the citrullination-induced aggregation of MOG31-55. Finally, a cytokine secretion assay was carried out on human monocyte-derived DCs, which showed the ability of the neoglycopeptide decorated with a single LeX to alter the balance of pro- and anti-inflammatory cytokines, inducing a tolerogenic response.