Zanamivir

Base Information

• Chemical Name: Zanamivir
• CAS No.: 139110-70-6
• Molecular Formula: C18H26 N2 O10
• Molecular Weight: 430.412
• Mol file: 139110-70-6.mol

Synonyms:D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID,5-(ACETYLAMINO)-4-[(AMINOIMINOMETHYL)AMINO]-2,6-ANHYDRO-3,4,5-TRIDEOXY;5-acetamido-4-amino-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate;methyl 5-acetamido-4-amino-7,8,9-tri-O-acetyl-2,3,4,5-tetradeoxy-D-glycero-D-galacto-non-2-enopyranosoate;5-(AcetylaMino)-4-aMino-2,6-anhydro-3,4,5-trideoxy;methyl 5-acetamido-4-amino-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate;methyl 5-acetamido-7,8,9-tri-O-acetyl-4-amino-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate;methyl 5-amino-4-(3-p-tolylureido)-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate;5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-amino-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester;D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID,5-(ACETYLAMINO)-4-AMINO-2,6-ANHYDRO-3,4,5-TRIDEOXY-,METHYL ESTER,7,8,9-TRIACETATE;

Chemical Property of Zanamivir

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >125°C (dec.)
• Boiling Point: 554.841oC at 760 mmHg
• Flash Point: 289.358oC
• PSA: 169.55000
• Density: 1.31g/cm3
• LogP: -0.20820
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Methanol, Water

Purity/Quality:

99% ^*data from raw suppliers

ZanamivirAmineTriacetateMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A synthetic precursor of Zanamivir (Z148000), as antiviral agents against influenza virus.

Technology Process of Zanamivir

There total 36 articles about Zanamivir 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: 100.0%

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5) → 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-amino-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester (139110-70-6)

Guidance literature:

With hydrogen; In ethanol; at 20 ℃; for 9h;

DOI:10.1016/j.bmc.2011.02.010

Reference yield:

C12H22N2O8*ClH (1360872-52-1) + acetic anhydride (108-24-7) → 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-amino-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester (139110-70-6)

Guidance literature:

C₁₂H₂₂N₂O₈*ClH; acetic anhydride; With sulfuric acid; at 20 ℃; Cooling with ice;

With ammonia; In methanol; water; pH=10;

DOI:10.1016/j.tet.2012.01.011

Reference yield:

N-acetyl neuraminic acid (19342-33-7) → 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-amino-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester (139110-70-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Dowex-50 (H+) / 40 - 45 °C

2.1: pyridine / 20 °C / Cooling with ice

3.1: trimethylsilyl trifluoromethanesulfonate / ethyl acetate / 3 h / 30 - 52 °C / Inert atmosphere

4.1: trimethylsilylazide / tert-butyl alcohol / Inert atmosphere; Reflux

4.2: 1 h

5.1: hydrogen; acetic acid / palladium 10% on activated carbon / toluene; methanol / 1 h

With pyridine; trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; hydrogen; acetic acid; palladium 10% on activated carbon; In methanol; ethyl acetate; toluene; tert-butyl alcohol;

upstream raw materials:

methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

N-acetylneuraminic acid methyl ester

methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl chloride

Downstream raw materials:

methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-(4'-hydroxyphenyl)acetamino-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate

methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-benzamido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate

methyl 5-acetamido-4-cyanamido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate

5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-(2-nitrobenzenesulfonamido)-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester