2,3,4,6-Tetra-O-acetyl-b-D-mannopyranosyl azide

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranosyl azide
• CAS No.: 65864-60-0
• Molecular Formula: C14H19N3O9
• Molecular Weight: 373.32
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID00428306
• Nikkaji Number: J1.267.173C
• Wikidata: Q82241128
• Mol file: 65864-60-0.mol

Synonyms:65864-60-0;2,3,4,6-Tetra-O-acetyl-b-D-mannopyranosyl azide;2,3,4,6-TETRA-O-ACETYL-BETA-D-MANNOPYRANOSYL AZIDE;[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-azidooxan-2-yl]methyl acetate;MFCD08703928;2,3,4,6-Tetra-O-acetyl--D-mannopyranosyl azide;ALPHA-D-MANNOPYRANOSYL AZIDE TETRAACETAT;SCHEMBL16246681;DTXSID00428306;AC6553;AKOS040767298;beta-D-Mannopyranosyl azide tetraacetate;AS-81997;1-Azido-1-deoxy-beta-D-mannopyranose tetraacetate;[(2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-azido-tetrahydropyran-2-yl]methyl acetate;(2R,3R,4S,5S,6R)-2-[(Acetyloxy)methyl]-6-azidooxane-3,4,5-triyl triacetate (non-preferred name)

Chemical Property of 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranosyl azide

Chemical Property:

• PSA: 164.18000
• LogP: -0.16744
• Storage Temp.: −20°C
• 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%min ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-b-D-mannopyranosyl azide ^*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)N=[N+]=[N-])OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@@H]([C@@H](O1)N=[N+]=[N-])OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranosyl azide

There total 12 articles about 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranosyl azide 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: 88.0%

per-O-acetyl-α-D-mannopyranose (4163-65-9) → 2,3,4,6-tetra-O-acetyl-1-azido-1-deoxy-β-D-mannopyranose (65864-60-0)

Guidance literature:

per-O-acetyl-α-D-mannopyranose; With trimethylsilyl iodide; In dichloromethane; for 0.5h; Heating;

With tetrabutylammoniun azide; In dichloromethane; for 0.166667h;

DOI:10.1016/S0008-6215(03)00042-9

Reference yield: 35.0%

D-Mannose (530-26-7) + acetic anhydride (108-24-7) → 2,3,4,6-tetra-O-acetyl-1-azido-1-deoxy-β-D-mannopyranose (65864-60-0)

Guidance literature:

D-Mannose; acetic anhydride; With iodine;

With hydrogen bromide; acetic acid; In dichloromethane;

With sodium azide; In N,N-dimethyl-formamide;

DOI:10.1021/acs.bioconjchem.9b00601

Reference yield: 33.0%

2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3) → 2,3,4,6-tetra-O-acetyl-1-azido-1-deoxy-β-D-mannopyranose (65864-60-0)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 15h; Inert atmosphere;

DOI:10.3762/bjoc.16.80

upstream raw materials:

acetobromomannose

per-O-acetyl-α-D-mannopyranose

D-Mannose pentaacetate

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

Downstream raw materials:

β-D-mannopyranosyl amine

N-(2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosyl)acetamide

Refernces

• 1、 Nerella, Srinivas,Kankala, Shravankumar,Gavaji, Brahmeshwari. "Synthesis of podophyllotoxin-glycosyl triazoles via click protocol mediated by silver (I)-N-heterocyclic carbenes and their anticancer evaluation as topoisomerase-II inhibitors". . p. 9 - 16. Retrieved 2019/06/27.
• 2、 Fan, Zhanfang,Guo, Chun,Hou, Zhuang,Li, Chuanchao,Lin, Bin,Liu, Yang,Liu, Yichuang,Wang, Yitong,Zhang, Miao. "Design, synthesis and biological evaluation of carbohydrate-based sulphonamide derivatives as topical antiglaucoma agents through selective inhibition of carbonic anhydrase II". . p. 383 - 390. Retrieved 2019/12/30.