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

Base Information

• Chemical Name: 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
• CAS No.: 581804-94-6
• Molecular Formula: C₅₄H₆₈N₄O₁₀
• Molecular Weight: 933.155

Synonyms:

Chemical Property of 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

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-[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

There total 6 articles about 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 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:

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) + 2-tri-n-butylstannylpyridine (17997-47-6) → 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[10.6.2.015,20]eicos-1(18)-en-5-yloxy}-6-methyl-tetrahydro-pyran-3-yl ester (581804-94-6,855476-98-1)

Guidance literature:

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; With tributyltin ethoxide; at 110 ℃;

p-(X-PhCH₂-X'); With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene;

2-tri-n-butylstannylpyridine; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene;

DOI:10.1016/j.bmcl.2005.03.011

Reference yield:

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-[4-(4-pyridin-2-yl-phenyl)-but-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 (581804-94-6,855476-98-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 75 percent / NCS; DMS; NEt₃ / CH₂Cl₂

2.1: Bu₃SnOEt / 110 °C

2.2: Pd(PPh₃)4 / toluene

2.3: Pd(PPh₃)4 / toluene

With N-chloro-succinimide; 2,3-dimercapto-succinic acid; tributyltin ethoxide; triethylamine; In dichloromethane; 1.1: Corey-Kim oxidation / 2.2: Stille coupling / 2.3: Stille coupling;

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-[4-(4-pyridin-2-yl-phenyl)-but-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 (581804-94-6,855476-98-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: DBU; DMAP / tetrahydrofuran; dimethylformamide

2.1: acetonitrile; H₂O

3.1: acetic acid / toluene

4.1: 82 percent / aq. HCl / ethanol / 48 h / 55 °C

5.1: 75 percent / NCS; DMS; NEt₃ / CH₂Cl₂

6.1: Bu₃SnOEt / 110 °C

6.2: Pd(PPh₃)4 / toluene

6.3: Pd(PPh₃)4 / toluene

With hydrogenchloride; dmap; N-chloro-succinimide; 2,3-dimercapto-succinic acid; tributyltin ethoxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 5.1: Corey-Kim oxidation / 6.2: Stille coupling / 6.3: Stille coupling;

DOI:10.1016/j.bmcl.2005.03.011

upstream raw materials:

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

2-tri-n-butylstannylpyridine

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

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