ethyl (3R,4S,5R)-5-azido-4-hydroxy-3-pentan-3-yloxycyclohexene-1-carboxylate

Base Information

• Chemical Name: ethyl (3R,4S,5R)-5-azido-4-hydroxy-3-pentan-3-yloxycyclohexene-1-carboxylate
• CAS No.: 204254-98-8
• Molecular Formula: C14H23N3O4
• Molecular Weight: 297.35000
• European Community (EC) Number: 805-633-3
• Mol file: 204254-98-8.mol

Synonyms:204254-98-8;ethyl (3R,4S,5R)-5-azido-4-hydroxy-3-pentan-3-yloxycyclohexene-1-carboxylate;SCHEMBL15481366;ethyl (3R,4S,5R)-5-azido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate;Ethyl(3R,4S,5R)-5-azido-3-(1-ethylpropoxy)-4-hydroxycyclohex-1-ene-1-carboxylate

Chemical Property of ethyl (3R,4S,5R)-5-azido-4-hydroxy-3-pentan-3-yloxycyclohexene-1-carboxylate

Chemical Property:

• PSA: 105.51000
• LogP: 1.94596
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 297.16885622
• Heavy Atom Count: 21
• Complexity: 428

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(CC)OC1C=C(CC(C1O)N=[N+]=[N-])C(=O)OCC
• Isomeric SMILES: CCC(CC)O[C@@H]1C=C(C[C@H]([C@@H]1O)N=[N+]=[N-])C(=O)OCC
• Uses: (3R,4S,5R)-Ethyl 5-azido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate is an intermediate in the synthesis of (1R,5R,6R)-5-(1-Ethylpropoxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylic Acid Ethyl Ester (E925510), an intermediate in the production of Oseltamivir.

Technology Process of ethyl (3R,4S,5R)-5-azido-4-hydroxy-3-pentan-3-yloxycyclohexene-1-carboxylate

There total 13 articles about ethyl (3R,4S,5R)-5-azido-4-hydroxy-3-pentan-3-yloxycyclohexene-1-carboxylate 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: 90.0%

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester (204254-96-6,1217834-81-5,1266663-89-1,2413185-89-2) → ethyl-(3R,4S,5R)-5-azido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate (204254-98-8)

Guidance literature:

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester; With water; ammonium chloride; In ethanol; for 0.333333h;

With sodium azide; In ethanol; at 68 ℃; for 14h;

DOI:10.1016/j.bmc.2012.01.026

Reference yield: 86.7%

C14H21N3O4 → C14H23N3O4 (204254-98-8)

Guidance literature:

With triethylsilane; titanium tetrachloride; In dichloromethane; at -5 - 0 ℃; for 8h;

Reference yield:

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester (204254-96-6,1217834-81-5,1266663-89-1,2413185-89-2) → ethyl (3R,4S,5R)-4-azido-3-(1-ethylpropoxy)-5-hydroxy-1-cyclohexene-1-carboxylate (204255-00-5) + ethyl-(3R,4S,5R)-5-azido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate (204254-98-8)

Guidance literature:

With sodium azide; ammonium chloride; In ethanol; water; at 70 - 75 ℃; for 18h; Yield given. Yields of byproduct given;

DOI:10.1021/jo980330q

upstream raw materials:

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate

ethyl (3aR,5S,7R,7aR)-5-hydroxy-7-methanesulfonyloxy-2,2-dimethylhexahydrobenzo[1,3]dioxole-5-carboxylate

Downstream raw materials:

ethyl-(1R,5R,6R)-5-(pentan-3-yloxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylate

(3R,4R,5S)-5-(acetylamino)-4-amino-3-(pentan-3-yloxy) cyclohex-1-ene-1-carboxylic acid

ethyl (3R,4R,5S)-5-azido-4-[(tert-butoxycarbonyl)amino]-3-(1-ethylpropoxy)cyclohex-1-ene-1-carboxylate

Refernces

• 1、 -. "Preparation method of oseltamivir enantiomer". . . Retrieved 2020/06/02.
• 2、 -. "METHOD FOR PREVENTING OR TREATING ARRHYTHMIA, METHOD FOR PREVENTING OR TREATING ATRIAL FIBRILLATION, MODEL OF SUSTAINED ATRIAL FIBRILLATION, METHOD FOR PRODUCING THE MODEL, AND METHOD FOR SCREENING FOR ATRIAL FIBRILLATION INHIBITOR". Paragraph 0098. . Retrieved 2014/03/24.