benzoic acid 4-dimethylamino-2-(11-ethyl-2,4,6,8,12,19-hexamethyl-7,9,14-trioxo-4-prop-2-ynyloxy-10,13-dioxa-15,18-diaza-tricyclo[10.6.2.0^15,20]eicos-1⁽¹⁸⁾-en-5-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: benzoic acid 4-dimethylamino-2-(11-ethyl-2,4,6,8,12,19-hexamethyl-7,9,14-trioxo-4-prop-2-ynyloxy-10,13-dioxa-15,18-diaza-tricyclo[10.6.2.0^15,20]eicos-1⁽¹⁸⁾-en-5-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 581804-84-4
• Molecular Formula: C₄₂H₅₉N₃O₁₀
• Molecular Weight: 765.945

Synonyms:

Chemical Property of benzoic acid 4-dimethylamino-2-(11-ethyl-2,4,6,8,12,19-hexamethyl-7,9,14-trioxo-4-prop-2-ynyloxy-10,13-dioxa-15,18-diaza-tricyclo[10.6.2.0^15,20]eicos-1⁽¹⁸⁾-en-5-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of benzoic acid 4-dimethylamino-2-(11-ethyl-2,4,6,8,12,19-hexamethyl-7,9,14-trioxo-4-prop-2-ynyloxy-10,13-dioxa-15,18-diaza-tricyclo[10.6.2.0^15,20]eicos-1⁽¹⁸⁾-en-5-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

There total 5 articles about benzoic acid 4-dimethylamino-2-(11-ethyl-2,4,6,8,12,19-hexamethyl-7,9,14-trioxo-4-prop-2-ynyloxy-10,13-dioxa-15,18-diaza-tricyclo[10.6.2.0^15,20]eicos-1⁽¹⁸⁾-en-5-yloxy)-6-methyl-tetrahydro-pyran-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: 75.0%

benzoic acid 4-dimethylamino-2-(11-ethyl-7-hydroxy-2,4,6,8,12,19-hexamethyl-9,14-dioxo-4-prop-2-ynyloxy-10,13-dioxa-15,18-diaza-tricyclo[10.6.2.015,20]eicos-1(18)-en-5-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester (581804-83-3,855476-82-3) → benzoic acid 4-dimethylamino-2-(11-ethyl-2,4,6,8,12,19-hexamethyl-7,9,14-trioxo-4-prop-2-ynyloxy-10,13-dioxa-15,18-diaza-tricyclo[10.6.2.015,20]eicos-1(18)-en-5-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester (581804-84-4,855476-83-4)

Guidance literature:

With N-chloro-succinimide; 2,3-dimercapto-succinic acid; triethylamine; In dichloromethane;

DOI:10.1016/j.bmcl.2005.03.011

Reference yield:

C57H81N3O15 → benzoic acid 4-dimethylamino-2-(11-ethyl-2,4,6,8,12,19-hexamethyl-7,9,14-trioxo-4-prop-2-ynyloxy-10,13-dioxa-15,18-diaza-tricyclo[10.6.2.015,20]eicos-1(18)-en-5-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester (581804-84-4,855476-83-4)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid / toluene

2: 82 percent / aq. HCl / ethanol / 48 h / 55 °C

3: 75 percent / NCS; DMS; NEt₃ / CH₂Cl₂

With hydrogenchloride; N-chloro-succinimide; 2,3-dimercapto-succinic acid; acetic acid; triethylamine; In ethanol; dichloromethane; toluene; 3: Corey-Kim oxidation;

DOI:10.1016/j.bmcl.2005.03.011

Reference yield:

6-O-propargyl-2'-O-benzoyl-4''-O-benzoylerythromycin (365568-75-8) → benzoic acid 4-dimethylamino-2-(11-ethyl-2,4,6,8,12,19-hexamethyl-7,9,14-trioxo-4-prop-2-ynyloxy-10,13-dioxa-15,18-diaza-tricyclo[10.6.2.015,20]eicos-1(18)-en-5-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester (581804-84-4,855476-83-4)

Guidance literature:

Multi-step reaction with 5 steps

1: DBU; DMAP / tetrahydrofuran; dimethylformamide

2: acetonitrile; H₂O

3: acetic acid / toluene

4: 82 percent / aq. HCl / ethanol / 48 h / 55 °C

5: 75 percent / NCS; DMS; NEt₃ / CH₂Cl₂

With hydrogenchloride; dmap; N-chloro-succinimide; 2,3-dimercapto-succinic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 5: Corey-Kim oxidation;

DOI:10.1016/j.bmcl.2005.03.011

upstream raw materials:

benzoic acid 4-dimethylamino-2-(11-ethyl-7-hydroxy-2,4,6,8,12,19-hexamethyl-9,14-dioxo-4-prop-2-ynyloxy-10,13-dioxa-15,18-diaza-tricyclo[10.6.2.0^15,20]eicos-1⁽¹⁸⁾-en-5-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

6-O-propargyl-2'-O-benzoyl-4''-O-benzoylerythromycin

C₅₇H₇₉N₃O₁₄

Downstream raw materials:

benzoic acid 4-dimethylamino-2-(11-ethyl-8-fluoro-2,4,6,8,12,19-hexamethyl-7,9,14-trioxo-4-prop-2-ynyloxy-10,13-dioxa-15,18-diaza-tricyclo[10.6.2.0^15,20]eicos-1⁽¹⁸⁾-en-5-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

benzoic acid 4-dimethylamino-2-{11-ethyl-2,4,6,8,12,19-hexamethyl-7,9,14-trioxo-4-[4-(4-thiophen-2-yl-phenyl)-but-2-ynyloxy]-10,13-dioxa-15,18-diaza-tricyclo[10.6.2.0^15,20]eicos-1⁽¹⁸⁾-en-5-yloxy}-6-methyl-tetrahydro-pyran-3-yl ester

benzoic acid 4-dimethylamino-2-{11-ethyl-2,4,6,8,12,19-hexamethyl-7,9,14-trioxo-4-[4-(4-pyridin-2-yl-phenyl)-but-2-ynyloxy]-10,13-dioxa-15,18-diaza-tricyclo[10.6.2.0^15,20]eicos-1⁽¹⁸⁾-en-5-yloxy}-6-methyl-tetrahydro-pyran-3-yl ester

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