51236-40-9

Basic information

• Product Name: N-ACETYL-1-CHLORO-3,4,6-TRI-O-ACETYL-GLUCOSAMINIDE
• Synonyms: N-ACETYL-1-CHLORO-3,4,6-TRI-O-ACETYL-GLUCOSAMINIDE;D-Glucopyranosyl chloride, 2-(acetylaMino)-2-deoxy-, 3,4,6-triacetate
• CAS NO: 51236-40-9
• Molecular Formula: C₁₄H₂₀ClNO₈
• Molecular Weight: 380.75496
• Mol File: 51236-40-9.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-ACETYL-1-CHLORO-3,4,6-TRI-O-ACETYL-GLUCOSAMINIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ACETYL-1-CHLORO-3,4,6-TRI-O-ACETYL-GLUCOSAMINIDE(51236-40-9)
• EPA Substance Registry System: N-ACETYL-1-CHLORO-3,4,6-TRI-O-ACETYL-GLUCOSAMINIDE(51236-40-9)

Safety Data

• Hazardous Substances Data: 51236-40-9(Hazardous Substances Data)

Upstream product

• 7512-17-6 N-Acetyl-D-glucosamine 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 66-84-2 D-(+)-glucosamine hydrochloride 
• 14131-68-1 N-acetyl-D-glucosamine 
• 75-34-3 1,1-dichloroethane 
• 14131-63-6 D-glucosamine hydrochloride 

Downstream Products

• 86520-53-8 2-[2-(2-Azidoethoxy)ethoxy]ethyl 3,4,6-tri-O-acetyl-2-N-acetamido-2-deoxy-β-D-glucopyranoside 
• 6205-69-2 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide 
• 94483-64-4 Pentyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 146288-30-4 pentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 1370339-20-0 Fmoc-D-Ser(Ac3GlcNAcβ)-OH 
• 160067-63-0 N^α-(9-flourenylmethoxycarbonyl)-3-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-Β-D-glucopyranosyl)-L-serine 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 29847-23-2 2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide 
• 131287-39-3 N^ω-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-N^α-(9-fluorenylmethyloxycarbonyl))-L-asparagine 
• 56343-03-4 8-methoxycarbonyloct-1-yl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 61145-38-8 S-cyanomethyl 2-N-acetamido-2-deoxy-1-thio-β-D-glucopyranoside 
• 61145-37-7 2-N-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio(S-cyanomethyl)-β-D-glucopyranoside 
• 74034-09-6 2-acetamido-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-glucitol 
• 20590-45-8 3,4,6-tri-O-acetyl-2-N-acetylamido-2-deoxy-β-D-glucopyranosyl isothiocyanate 

Relevant articles and documents

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.

DRUG DELIVERY

A drug delivery vehicle comprising a vesicle conjugated to one or more targeting groups, wherein the targeting groups comprise an oligosaccharide which is Lewis A or Lewis B or a mimetic thereof, or a pharmaceutically acceptable salt or PEGylated form of the oligosaccharide : (I) wherein R represents the pointof attachment to the vesicle.10

Synthesis and biological evaluation of novel C1-glycosyl thiazole derivatives as acetylcholinesterase inhibitors

A new series of C1-glycosyl thiazole derivatives was synthesised by the reaction of 1-(1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranos-2-yl)thiourea with 2-bromoacetophenone derivatives. Subsequent removal of the acetyl groups were conducted using NaOMe-MeOH. The structures of all new products were confirmed by IR, 1H NMR and HRMS (ESI). The acetylcholinesterase inhibitory activities of these new compounds were tested. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(4-nitrophenyl)-1,3-thiazole-2-amine showed the best activity with an inhibition rate of 43.21%.