1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-mannopyranose

Base Information

• Chemical Name: 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-mannopyranose
• CAS No.: 68733-20-0
• Molecular Formula: C14H19 N3 O9
• Molecular Weight: 373.32
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID60461456
• Nikkaji Number: J2.262.284F
• Wikidata: Q82285807
• Mol file: 68733-20-0.mol

Synonyms:1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-alpha-D-mannopyranose;1,3,4,6-tetra-O-acetyl-2-azido-2-deoxymannopyranose;4AcN3dManp

Chemical Property of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-mannopyranose

Chemical Property:

• Melting Point: 132 °C
• PSA: 164.18000
• LogP: -0.16744
• Storage Temp.: Refrigerator
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 373.11212919
• Heavy Atom Count: 26
• Complexity: 617

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-a-D-mannopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=O)C)N=[N+]=[N-])OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)OC(=O)C)N=[N+]=[N-])OC(=O)C)OC(=O)C
• Description: 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranose is an analog of N-acetylmannosamine (ManNAc) and a building block. It has been used as a precursor in the synthesis of differently substituted trimers of the group A N. meningitidis capsular polysaccharide repeating unit for use in immunological experiments. It has also been used in the synthesis of fluorescent probes for lysosomal labeling.

Technology Process of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-mannopyranose

There total 17 articles about 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-mannopyranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

acetic anhydride (108-24-7) + methyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside (115945-97-6) → 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside (68733-20-0)

Guidance literature:

With sulfuric acid; at 0 ℃; for 1h;

DOI:10.1135/cccc20030801

Reference yield: 85.0%

acetic anhydride (108-24-7) + (4aR,6S,7S,8R,8aS)-7-azido-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-ol → 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside (68733-20-0)

Guidance literature:

With sulfuric acid; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jacs.1c06778

Reference yield: 78.0%

acetic anhydride (108-24-7) + Methyl 2-azido-2-deoxy-4,6-O-(phenylmethylene)-α-D-mannopyranoside (116003-78-2) → 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside (68733-20-0)

Guidance literature:

With sulfuric acid; at 20 ℃; for 2.5h;

DOI:10.1039/b807016d

upstream raw materials:

mercury(II) diacetate

D-glucal triacetate

sodium acetate

acetic anhydride

Downstream raw materials:

4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside

Benzyl-2-amino-2-desoxy-α-D-mannopyranosid

phenylmethyl 2-acetylamino-2-deoxy-α-D-mannopyranoside

Benzyl-2-<(benzyloxycarbonyl)amino>-2-desoxy-α-D-mannopyranosid

Refernces

• 1、 Abreu Mota, Tiago,Aliu, Butrint,Cattaneo, Ivan,Ciancaglini, Matias,Cramer, Jonathan,Ernst, Beat,Jakob, Roman P.,Jiang, Xiaohua,Klein, Sebastian,Lakkaichi, Adem,Maier, Timm,Rabbani, Said,Schwardt, Oliver,Zimmer, Gert. "Sweet Drugs for Bad Bugs: A Glycomimetic Strategy against the DC-SIGN-Mediated Dissemination of SARS-CoV-2". . p. 17465 - 17478. Retrieved 2021/11/04.
• 2、 Medve, Laura,Achilli, Silvia,Guzman-Caldentey, Joan,Thépaut, Michel,Senaldi, Luca,Le Roy, Aline,Sattin, Sara,Ebel, Christine,Vivès, Corinne,Martin-Santamaria, Sonsoles,Bernardi, Anna,Fieschi, Franck. "Enhancing Potency and Selectivity of a DC-SIGN Glycomimetic Ligand by Fragment-Based Design: Structural Basis". . p. 14659 - 14668. Retrieved 2019/11/11.