67817-30-5

Usage

Uses

Used in Pharmaceutical Industry:
1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose is used as a building block for the synthesis of glycoconjugates, which are molecules composed of a carbohydrate linked to another type of molecule, such as proteins, lipids, or other carbohydrates. These glycoconjugates play crucial roles in various biological processes, including cell recognition, signal transduction, and immune responses. The ability to modify and couple 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose to other molecules makes it a valuable tool in the development of new drugs and therapeutic agents.
Used in Drug Delivery Systems:
1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose is used as a component in the design of drug delivery systems. Its unique structure and functional groups can be exploited to create targeted drug delivery systems, which can improve the efficacy and reduce the side effects of drugs. For example, 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose can be used to conjugate drugs to specific targeting molecules, such as antibodies or peptides, to enhance their delivery to diseased cells or tissues.
Used in Chemical Research:
1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose is used as a research tool in the study of complex carbohydrate structures and their biological functions. Its unique structure and reactivity make it an ideal candidate for investigating the role of carbohydrates in various biological processes and diseases. Researchers can use 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose to probe the interactions between carbohydrates and other biomolecules, such as proteins and lipids, and to develop new methods for the synthesis and modification of carbohydrate-containing compounds.

InChI:InChI=1/C14H19N3O9/c1-6(18)22-5-10-12(23-7(2)19)13(24-8(3)20)11(16-17-15)14(26-10)25-9(4)21/h10-14H,5H2,1-4H3/t10-,11-,12+,13-,14+/m1/s1

Upstream product

• 68733-05-1 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl nitrate 
• 10387-40-3 potassium thioacetate 
• 68733-26-6 2-azido-2-deoxy-D-galactose 
• 108-24-7 acetic anhydride 
• 127-09-3 sodium acetate 
• 196398-25-1 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α/β-D-galactopyranosyl nitrate 
• 1666-13-3 diphenyl diselenide 
• 4098-06-0 triacetyl-D-galactal 
• 1772-03-8 D-(+)-galactosamine hydrochloride 
• 68733-26-6 2-deoxy-2-azidogalactopyranose 
• 68733-06-2 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl nitrate 
• 84278-00-2 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose 

Downstream Products

• 67673-39-6 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide 
• 114643-38-8 tert-butyl p-(2-acetamido-3,4,6-tri-O-acetyl-α-D-galactopyranosyloxy)cinnamate 
• 114643-39-9 p-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyloxy)cinnamic acid 
• 114643-42-4 N¹-p-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyloxy)cinnamoyl-N²,N³-di-tert-butoxycarbonylspermidine 
• 114643-54-8 N¹-cinnamoylspermidine dihydrochloride 
• 114656-12-1 N¹-p-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyloxy)cinnamoyl-N²,N³-di-tert-butoxycarbonylspermidine 
• 114643-29-7 tert-butyl p-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyloxy)cinnamate 
• 114643-37-7 p-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyloxy)cinnamic acid 
• 114643-46-8 (E)-3-[4-((2R,3R,4R,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-amino-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester 
• 114643-47-9 (E)-3-[4-((2R,3R,4R,5R,6R)-3-Amino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester 
• 83021-94-7 ethyl p-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyloxy)cinnamate 
• 819798-40-8 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside 
• 500213-00-3 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-galactopyranoside 
• 819798-39-5 phenyl-2-azido-2-deoxy-1-thio-β-D-galactopyranoside 

Relevant academic research and scientific papers

Immunological response from an entirely carbohydrate antigen: Design of synthetic vaccines based on Tn-PS A1 conjugates

(Figure Presented) An entirely carbohydrate-based immunogen consisting of a zwitterionic polysaccharide (ZPS) PS A1 and the well-known tumor antigen Tn has been designed, synthesized, and studied for immunological effects. The PS A1 motif was included to act as an MHCII elicitor for a T-cell-dependent immune response with increased immunogenicity against tumor-associated carbohydrate antigens, providing an alternative to carrier proteins. Through the use of C57BL/6 mice, it has been shown that chemical modification of PS A1 does not alter the recognition sequence responsible for an MHCII-mediated, T-cell-dependent immune response. The Tn-PS A1 conjugate construct confers specificity toward the Tn antigen alone, and specific carbohydrate immunoglobulins, namely, IgG3, are generated from intraperitoneal immunizations with or without adjuvant. The properties of the vaccine candidate are attributed to a site-specific linking strategy that incurs significant incorporation of Tn antigen.

Safe and Scalable Continuous Flow Azidophenylselenylation of Galactal to Prepare Galactosamine Building Blocks

Differentially protected galactosamine building blocks are key components for the synthesis of human and bacterial oligosaccharides. The azidophenylselenylation of 3,4,6-tri-O-acetyl-d-galactal provides straightforward access to the corresponding 2-nitrog

Synthesis of trisaccharide repeating unit of fucosylated chondroitin sulfate

We described the chemical synthesis of a sulfated trisaccharide repeating unit of fucosylated chondroitin sulfate (FCS), which has significant anticoagulant activity. Well-functionalized monosaccharides were readily prepared, and highly efficient glycosyl

A stereoselective and flexible synthesis to access both enantiomers of N-acetylgalactosamine and peracetylated N-acetylidosamine

Synthetic approaches towards N-acetylgalactosamine (GalNAc) have been attracting considerable interest since this compound is known for its pivotal role in cell-cell interaction and receptor induced cell signaling. Herein, we present a synthetic route in which two of the four stereogenic centers present in the target compound are derived from enantiopure tartaric acid being selectively converted to epoxy alcohols. The key step is the Pd-catalyzed, stereo- and regioselective epoxide opening and subsequent nucleophilic substitution of an azide functionality. This approach enables the synthesis of the naturally D- and unnaturally L-configured GalNAc, as well as both enantiomers of the largely unknown N-acetylidosamine (IdoNAc).

Synthetic and immunological studies on trimeric MUC1 immunodominant motif antigen-based anti-cancer vaccine candidates

Therapeutic vaccines have been regarded as a very promising treatment modality against cancer. Tumor-associated MUC1 is a promising antigen for the design of antitumor vaccines. However, body's immune tolerance and low immunogenicity of MUC1 glycopeptides

A Modular Approach to the Total Synthesis of Tunicamycins

The tunicamycins constitute a delicate mimic of the bisubstrate intermediates of N-acetyl-D-hexosamine-1-phosphate translocases and thus inhibit bacterial cell-wall synthesis and the N glycosylation of eukaryotic proteins. An efficient approach to the synthesis of this unique type of nucleoside antibiotics is now reported and features the assembly of five modules in a highly stereoselective and robust manner. A Mukaiyama aldol reaction, intramolecular acetal formation, gold(I)-catalyzed O and N glycosylation, and final Nacylation were used as the key steps. The modular and stereoselective synthesis of tunicamycins features a Mukaiyama aldol reaction, intramolecular acetal formation, gold(I)-catalyzed O and N glycosylation, and final N acylation as the key steps. These natural products are a unique type of nucleoside antibiotics with potent inhibitory activities against bacterial cell-wall synthesis and the N-glycosylation of eukaryotic proteins.

Cytotoxic properties of d-gluco-, d-galacto- and d-manno-configured 2-amino-2-deoxy-glycerolipids against epithelial cancer cell lines and BT-474 breast cancer stem cells

Glycosylated antitumor ether lipids (GAELs) 6 and 7 containing a α- or β-d-gluco-configured 2-amino-2-deoxy (2-NH2-Glc) sugar moiety linked to a glycerolipid aglycone kill cancer cell lines via a non-apoptotic mechanism that could be exploited

Synthesis of peptides and glycopeptides with polyproline II helical topology as potential antifreeze molecules

A library of peptides and glycopeptides containing (4R)-hydroxy-l-proline (Hyp) residues were designed with a view to providing stable polyproline II (PPII) helical molecules with antifreeze activity. A library of dodecapeptides containing contiguous Hyp

Synthesis of an isotopically-labelled antarctic fish antifreeze glycoprotein probe

Antifreeze glycoproteins (AFGPs) are glycosylated polypeptides produced by Antarctic and Arctic fishes, which allow them to survive in seawater at sub-zero temperatures. An investigation into the postulated enteric uptake of AFGP synthesized in the exocrine pancreas of Antarctic fishes required a custom-prepared AFGP probe that incorporated seven isotopically-labelled Ala residues for detection by mass spectrometry. The AFGPs are composed of a repetitive three amino acid unit (Ala-Ala-Thr), in which the threonine residue is glycosylated with the disaccharide β-d-Gal-(1→3) α-d-GalNAc. The synthesis of isotopically-labelled AFGP8 (1), as well as the optimized synthesis of the protected glycosylated amino acid building block 2, is reported.

Microwave-assisted synthesis of fluorescein-labelled GalNAcα1-O-Ser/ Thr (Tn) glycopeptides as immunological probes

Fluorescently labelled glycopeptides containing GalNAcα1-O-Ser/Thr residues provide valuable immunological probes for the development of cancer vaccines. The microwave-assisted automated Fmoc solid-phase synthesis of a series of 5(6)-carboxyfluorescein-labelled GalNAcα1-O-Ser/Thr peptides is described. Lys(Dde)-Gly-Wang polystyrene resin was elongated using Fmoc SPPS with incorporation of several GalNAcα1-O-Ser/Thr residues. Deprotection of the Lys(Dde) then allowed attachment of the 5(6)-carboxyfluorescein label. The synthetic methodology described is flexible and suitably robust enabling the incorporation of three contiguous GalNAcα1-O-Ser residues into the peptide chain. Georg Thieme Verlag Stuttgart · New York.