214467-60-4

Usage

Uses

Used in Pharmaceutical Industry:
2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-beta-D-glucopyranosyl Azide is used as a key intermediate in the synthesis of nonglycosylated and glycosylated androgenic gland hormone (AGH) for the pharmaceutical industry. The compound plays a crucial role in the preparation of AGH with N-linked glycan using expressed protein ligation, which is essential for the development of novel therapeutic agents targeting hormonal imbalances and related conditions.
Used in Chemical Research:
In the field of chemical research, 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-beta-D-glucopyranosyl Azide serves as a valuable compound for studying the chemical properties and reactivity of glycosyl azides. Researchers can use 2-ACETAMIDO-3,4,6-TRI-O-BENZYL-2-DEOXY-BETA-D-GLUCOPYRANOSYL AZIDE to explore new synthetic pathways, develop innovative methodologies, and gain insights into the structural and functional aspects of various biologically active molecules.
Used in Material Science:
2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-beta-D-glucopyranosyl Azide can also be employed in material science for the development of novel biomaterials and drug delivery systems. The compound's unique chemical properties and reactivity make it a promising candidate for the design and synthesis of advanced materials with tailored properties for various applications, including drug delivery, tissue engineering, and diagnostics.

InChI:InChI=1/C29H32N4O5/c1-21(34)31-26-28(37-19-24-15-9-4-10-16-24)27(36-18-23-13-7-3-8-14-23)25(38-29(26)32-33-30)20-35-17-22-11-5-2-6-12-22/h2-16,25-29H,17-20H2,1H3,(H,31,34)/t25-,26-,27-,28-,29-/m1/s1

Upstream product

• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 13435-12-6 N-Trimethylsilylacetamide 
• 108-24-7 acetic anhydride 
• 214467-64-8 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 168644-99-3 ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 115533-35-2 ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 29847-23-2 2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide 

Downstream Products

• 219968-28-2 (S)-N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-2-tert-butoxycarbonylamino-succinamic acid benzyl ester 
• 522634-52-2 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosylamine 
• 1139906-45-8 N2-(9-fluorenylmethoxycarbonyl)-N4-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-L-aspargine tert-butyl ester 
• 522634-59-9 N-{2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl}-3-(benzyloxycarbonylamino)propanoic acid amide 
• 522634-53-3 2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide 
• 522634-54-4 2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosylamine 
• 522634-55-5 2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranose 

Relevant academic research and scientific papers

Synthesis and antibacterial activities of N-Glycosylated derivatives of tyrocidine a, a macrocyclic peptide antibiotic

An efficient and practical method for macrocyclic glycopeptide synthesis was developed and utilized to synthesize tyrocidine A and its glycosylated derivatives. The method is based on solid-phase peptide synthesis using 2-chlorotrityl resin as the solid-phase support and glycosyl amino acids as building blocks. After glycopeptides with fully protected glycans and side chains were released from the acid-labile resin, their Cand N-termini were intramolecularly coupled in solution to afford cyclic glycopeptides in quantitative yields. This synthetic method should be generally applicable to various macrocyclic glycopeptides. Biological studies of the synthetic tyrocidine A derivatives showed that linking glycans directly to the Asn residue of tyrocidine A diminished its antibacterial activity, but linking glycans to Asn via a simple spacer did not. These results Revealed the important impact of glycans on the activities, and probably the structures, of glycopeptide antibiotics.

Synthesis and conformational analysis of pseudosugar analogues of chitotriose

EDC mediated coupling of the 4-O-succinoyl glycosyl azide 2 with glycosylamine 3 gave the protected glycosylazide 4. Hydrogenation of 4 afforded the glycosylamine 5. Chemoselective hydrolysis of the reducing end glycosylamine, followed by hydrogenation af

C2-amidoglycosylation. Scope and mechanism of nitrogen transfer

A one-pot C2-amidoglycosylation reaction for the synthesis of 2-N-acyl-2-deoxy-β-pyranosides from glycals is described. Glycal donors activated by the reagent combination of thianthrene-5-oxide (11) and Tf2O, followed by treatment with an amide nucleophile and a glycosyl acceptor, lead to the formation of various C2-amidoglycoconjugates. Both the C2-nitrogen transfer and the glycosidic bond formation proceed stereoselectively, allowing for the introduction of both natural and nonnatural amide functionalities at C2 with concomitant anomeric bond formation in a one-pot procedure. Tracking of the reaction by low-temperature NMR spectroscopy employing 15N- and 18O-isotope labels suggests a mechanism involving the formation of the C2-sulfonium glycosyl imidate 39 as well as oxazoline 37 as key intermediates in this novel oxidative glycosylation process.

Synthesis of fully and partially benzylated glycosyl azides via thioalkyl glycosides as precursors for the preparation of N-glycopeptides

Fully O-benzylated mono-, di- and trisaccharide glycosyl azides representing the reducing terminal of the core structure of N-glycans were synthesized. Totally and partially benzylated thioalkyl glucosamine glycosides were converted into the corresponding