41355-44-6

Basic information

• Product Name: 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE
• Synonyms: ALPHA-ACETOCHLORO-D-GALACTOSAMINE;ACETOCHLORO-ALPHA-D-GALACTOSAMINE;2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE;2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-ù-D-galactopyranosyl chloride;N,3,4,6-O-Tetraacetyl-α-D-galactosaMinyl Chloride;2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-a-D-galactopyranosyl chloride
• CAS NO: 41355-44-6
• Molecular Formula: C₁₄H₂₀ClNO₈
• Molecular Weight: 365.76
• Mol File: 41355-44-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 131-136 °C (decomp)
• Boiling Point: 516.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• PKA: 13.22±0.70(Predicted)
• CAS DataBase Reference: 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE(41355-44-6)
• EPA Substance Registry System: 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE(41355-44-6)

Safety Data

• Hazardous Substances Data: 41355-44-6(Hazardous Substances Data)

Usage

Description

2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE is a complex organic compound that serves as an essential building block in the synthesis of various biologically active molecules, particularly in the field of glycobiology. It is characterized by its unique structure, which includes an acetamido group, a deoxy sugar, and three acetyl groups attached to specific carbon positions, as well as a reactive chloro group that allows for further chemical modifications.

Uses

Used in Pharmaceutical Industry:
2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE is used as a key intermediate in the synthesis of various glycoconjugates, such as selenenylsulfide-linked glycopeptides and glycoproteins. These molecules play crucial roles in numerous biological processes, including cell adhesion, immune response, and cell signaling, making them valuable targets for drug development.
Used in Research and Development:
In the field of research, 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE is employed as a versatile building block for the preparation of diverse glycoconjugates with potential applications in studying carbohydrate recognition, protein-carbohydrate interactions, and the development of novel bioactive compounds.
Used in Diagnostics:
2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE can also be utilized in the development of diagnostic tools, such as glycan-based assays and sensors, which can detect and monitor various diseases and conditions by recognizing specific carbohydrate structures on the surface of cells or in biological fluids.
Used in Material Science:
2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL CHLORIDE may find applications in the development of carbohydrate-based materials, such as hydrogels, nanoparticles, and self-assembled structures, which can be used in drug delivery, tissue engineering, and other biomedical applications due to their unique properties and biocompatibility.

Upstream product

• 72-87-7 N-acetyl-D-galactosamine 
• 75-36-5 acetyl chloride 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 75-34-3 1,1-dichloroethane 
• 14131-63-6 D-glucosamine hydrochloride 
• 108-24-7 acetic anhydride 
• 66-84-2 D-(+)-glucosamine hydrochloride 
• 14131-68-1 N-acetyl-D-glucosamine 

Downstream Products

• 13089-70-8 phenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 110253-00-4 tetra-O-acetyl-2-amino-2-deoxy-α-D-galactopyranose; hydrochloride 
• 124167-46-0 4-methylumbelliferyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside 
• 36476-29-6 4-methylumbelliferyl 2-acetamido-2-deoxy-β-D-galactopyranoside 
• 22256-76-4 methyl 2-acetamido-2-deoxy-β-D-galactopyranoside 
• 4291-19-4 phenyl 2-acetamido-2-deoxy-β-D-galactopyranoside 
• 56343-03-4 8-methoxycarbonyloct-1-yl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 6205-69-2 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide 
• 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 
• 41355-94-6 benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside 
• 51450-09-0 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose 
• 1338496-31-3 2-(4-benzyloxyphenyl)ethyl 2-acetamido-2-deoxy-β-D-glucopyranoside 

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%.