Zanamivir Azide Triacetate Methyl Ester

Base Information

• Chemical Name: Zanamivir Azide Triacetate Methyl Ester
• CAS No.: 130525-58-5
• Molecular Formula: C18H24N4O10
• Molecular Weight: 456.409
• European Community (EC) Number: 603-423-4
• Nikkaji Number: J889.170B
• Mol file: 130525-58-5.mol

Synonyms:130525-58-5;Zanamivir Azide Triacetate Methyl Ester;D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID;D-glycero-D-galacto-Non-2-enonic acid, 5-(acetylamino)-2,6-anhydro-4-azido-3,4,5-trideoxy-, methyl ester, 7,8,9-triacetate;methyl (2R,3R,4S)-3-acetamido-4-azido-2-[(1S,2R)-1,2,3-triacetyloxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate;(1S,2R)-1-((2R,3R,4S)-3-acetamido-4-azido-6-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate;SCHEMBL15045962;MFCD08704809;AS-76958;CS-0081277;D95530;Q-102537;Methyl 7,8,9-tri-o-acetyl-N-acetyl-2-deoxy-2,3-didehydro-4a-azido-D-neuraminate;(4S,5R,6R)-5-ACETYLAMINO-4-AZIDO-6-(1S,2R,3-TRIACETOXYPROPYL)-5,6-DIHYDRO-4H-PYRAN-2-CARBOXYLIC ACID;4-Azido-2,4-dideoxy-2,3-didehydro-7-O,8-O,9-O,N-tetraacetyl-alpha-neuraminic acid methyl ester;5-(Acetylamino)-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic Acid Methyl Ester 7,8,9-Triacetate;Methyl 5-acetamido-7,8,9-O-triacetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonat

Chemical Property of Zanamivir Azide Triacetate Methyl Ester

Chemical Property:

• Appearance/Colour: Off-white solid
• PSA: 193.28000
• LogP: -0.10414
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Methanol
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 13
• Exact Mass: 456.14924298
• Heavy Atom Count: 32
• Complexity: 836

Purity/Quality:

99% ^*data from raw suppliers

Zanamivir Azide Triacetate Methyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C=C(OC1C(C(COC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)N=[N+]=[N-]
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H](C=C(O[C@H]1[C@@H]([C@@H](COC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)N=[N+]=[N-]
• Uses: D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID is an intermediate used in the preparation of Zanamivir derivatives.

Technology Process of Zanamivir Azide Triacetate Methyl Ester

There total 49 articles about Zanamivir Azide Triacetate Methyl Ester 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: 98.0%

methyl (5-acetamido-7,8,9-tri-O-acetyl-4-azido-3,4,5-trideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)onate chloride (163860-77-3) → methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 10 ℃; for 1h;

DOI:10.1021/ol0491890

Reference yield: 96.0%

methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate (78850-37-0) → methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5)

Guidance literature:

With trimethylsilylazide; In tert-butyl alcohol; for 10h; Inert atmosphere; Reflux;

Reference yield: 87.0%

Methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-talo-non-2-enonate (80973-54-2) → methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate (130525-58-5)

Guidance literature:

With diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; for 23h; Ambient temperature;

upstream raw materials:

Methyl 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-3,5-dideoxy-D-glycero-D-talo-non-2-enonate

methyl (3aS,4R,7aR)-4-[(1S,2R)-1,2,3-triacetoxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate

methyl (methyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-3,4,5-trideoxy-2-thio-D-glycero-α-D-galacto-nonulopyranosid)onate

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Downstream raw materials:

zanamivir

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-cyclohexenyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-phenyl-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-[2-(4-fluorophenyl)-N'-(methylsulfonyl)acetimidamido]-D-glycero-D-galacto-non-2-enonate

Refernces

• 1、 Itzstein, Mark von,Jin, Betty,Wu, Wen-Yang,Chandler, Malcolm. "A convenient method for the introduction of nitrogen and sulfur at C-4 on a sialic acid analogue". . p. 181 - 186. Retrieved 1993.
• 2、 -. "N-ACETYLATED SIALIC ACIDS AND RELATED SIALOSIDES". Paragraph 0268; 0269. . Retrieved 2018/06/12.
• 3、 -. "FATTY ACID ANTIVIRAL CONJUGATES AND THEIR USES". Paragraph 0755; 0763. . Retrieved 2016/06/01.