Imidazole-1-carboxylic acid (E)-(2R,3S,7R,9R,10R,11R,13R)-9-allyloxy-10-((2S,3R,4S,6R)-3-benzoyloxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,5,7,9,11,13-hexamethyl-6,12,14-trioxo-oxacyclotetradec-4-en-3-yl ester

Base Information

Chemical Name:Imidazole-1-carboxylic acid (E)-(2R,3S,7R,9R,10R,11R,13R)-9-allyloxy-10-((2S,3R,4S,6R)-3-benzoyloxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,5,7,9,11,13-hexamethyl-6,12,14-trioxo-oxacyclotetradec-4-en-3-yl ester
CAS No.:205110-40-3
Molecular Formula:C₄₃H₅₉N₃O₁₁
Molecular Weight:793.955
Hs Code.:

Imidazole-1-carboxylic acid (E)-(2R,3S,7R,9R,10R,11R,13R)-9-allyloxy-10-((2S,3R,4S,6R)-3-benzoyloxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,5,7,9,11,13-hexamethyl-6,12,14-trioxo-oxacyclotetradec-4-en-3-yl ester

Synonyms:Imidazole-1-carboxylic acid (E)-(2R,3S,7R,9R,10R,11R,13R)-9-allyloxy-10-((2S,3R,4S,6R)-3-benzoyloxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,5,7,9,11,13-hexamethyl-6,12,14-trioxo-oxacyclotetradec-4-en-3-yl ester

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Chemical Property of Imidazole-1-carboxylic acid (E)-(2R,3S,7R,9R,10R,11R,13R)-9-allyloxy-10-((2S,3R,4S,6R)-3-benzoyloxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,5,7,9,11,13-hexamethyl-6,12,14-trioxo-oxacyclotetradec-4-en-3-yl ester

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Technology Process of Imidazole-1-carboxylic acid (E)-(2R,3S,7R,9R,10R,11R,13R)-9-allyloxy-10-((2S,3R,4S,6R)-3-benzoyloxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,5,7,9,11,13-hexamethyl-6,12,14-trioxo-oxacyclotetradec-4-en-3-yl ester

There total 8 articles about Imidazole-1-carboxylic acid (E)-(2R,3S,7R,9R,10R,11R,13R)-9-allyloxy-10-((2S,3R,4S,6R)-3-benzoyloxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,5,7,9,11,13-hexamethyl-6,12,14-trioxo-oxacyclotetradec-4-en-3-yl 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: 68.0%

: 530-62-1
1,1'-carbonyldiimidazole

: 205109-97-3
Benzoic acid (2S,3R,4S,6R)-2-((3R,5R,6R,7R,9R,11R,12R,13S,14R)-7-allyloxy-14-ethyl-12,13-dihydroxy-3,5,7,9,11,13-hexamethyl-2,4,10-trioxo-oxacyclotetradec-6-yloxy)-4-dimethylamino-6-methyl-tetrahydro-pyran-3-yl ester

: 205110-40-3
Imidazole-1-carboxylic acid (E)-(2R,3S,7R,9R,10R,11R,13R)-9-allyloxy-10-((2S,3R,4S,6R)-3-benzoyloxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,5,7,9,11,13-hexamethyl-6,12,14-trioxo-oxacyclotetradec-4-en-3-yl ester

Guidance literature:: With lithium hydride; In tetrahydrofuran; at 20 ℃; for 168h;
DOI:10.1021/jm0102349

Reference yield:

: 93-97-0
benzoic acid anhydride

: 205110-40-3
Imidazole-1-carboxylic acid (E)-(2R,3S,7R,9R,10R,11R,13R)-9-allyloxy-10-((2S,3R,4S,6R)-3-benzoyloxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,5,7,9,11,13-hexamethyl-6,12,14-trioxo-oxacyclotetradec-4-en-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 2.46 g / Et₃N / CH₂Cl₂ / 24 h / 20 °C

2: 77 percent / NCS; Me₂S / CH₂Cl₂ / 0.5 h / -10 - -5 °C

3: 68 percent / LiH / tetrahydrofuran / 168 h / 20 °C

With N-chloro-succinimide; dimethylsulfide; lithium hydride; triethylamine; In tetrahydrofuran; dichloromethane; 2: Corey-Kim oxidation;
DOI:10.1021/jm0102349

Reference yield:

: 198482-51-8
6-O-allylerythromycin A

: 205110-40-3
Imidazole-1-carboxylic acid (E)-(2R,3S,7R,9R,10R,11R,13R)-9-allyloxy-10-((2S,3R,4S,6R)-3-benzoyloxy-4-dimethylamino-6-methyl-tetrahydro-pyran-2-yloxy)-2-ethyl-3,5,7,9,11,13-hexamethyl-6,12,14-trioxo-oxacyclotetradec-4-en-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 3.11 g / aq. HCl / ethanol / 10 h / 20 °C

2: 2.46 g / Et₃N / CH₂Cl₂ / 24 h / 20 °C

3: 77 percent / NCS; Me₂S / CH₂Cl₂ / 0.5 h / -10 - -5 °C

4: 68 percent / LiH / tetrahydrofuran / 168 h / 20 °C

With hydrogenchloride; N-chloro-succinimide; dimethylsulfide; lithium hydride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; 3: Corey-Kim oxidation;
DOI:10.1021/jm0102349