Benzoic acid (2S,3R,4S,6R)-2-{(3R,5R,6R,7R,9R,11R,12R,13S,14R)-7-[(E)-3-(4-chloro-phenyl)-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

Base Information

• Chemical Name: Benzoic acid (2S,3R,4S,6R)-2-{(3R,5R,6R,7R,9R,11R,12R,13S,14R)-7-[(E)-3-(4-chloro-phenyl)-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
• CAS No.: 1053248-32-0
• Molecular Formula: C₄₅H₆₂ClNO₁₁
• Molecular Weight: 828.44

Synonyms:Benzoic acid (2S,3R,4S,6R)-2-{(3R,5R,6R,7R,9R,11R,12R,13S,14R)-7-[(E)-3-(4-chloro-phenyl)-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

Chemical Property of Benzoic acid (2S,3R,4S,6R)-2-{(3R,5R,6R,7R,9R,11R,12R,13S,14R)-7-[(E)-3-(4-chloro-phenyl)-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

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (2S,3R,4S,6R)-2-{(3R,5R,6R,7R,9R,11R,12R,13S,14R)-7-[(E)-3-(4-chloro-phenyl)-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

There total 8 articles about Benzoic acid (2S,3R,4S,6R)-2-{(3R,5R,6R,7R,9R,11R,12R,13S,14R)-7-[(E)-3-(4-chloro-phenyl)-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 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:

1-Chloro-4-iodobenzene (637-87-6) + 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 (205109-97-3) → Benzoic acid (2S,3R,4S,6R)-2-{(3R,5R,6R,7R,9R,11R,12R,13S,14R)-7-[(E)-3-(4-chloro-phenyl)-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 (1053248-32-0)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In acetonitrile; at 60 - 80 ℃; for 12.5h;

DOI:10.1021/jm0102349

Reference yield:

benzoic acid anhydride (93-97-0) → Benzoic acid (2S,3R,4S,6R)-2-{(3R,5R,6R,7R,9R,11R,12R,13S,14R)-7-[(E)-3-(4-chloro-phenyl)-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 (1053248-32-0)

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: Pd(OAc)2; Ph₃P; Et₃N / acetonitrile / 12.5 h / 60 - 80 °C

With palladium diacetate; N-chloro-succinimide; dimethylsulfide; triethylamine; triphenylphosphine; In dichloromethane; acetonitrile; 2: Corey-Kim oxidation / 3: Heck coupling;

DOI:10.1021/jm0102349

Reference yield:

6-O-allylerythromycin A (198482-51-8) → Benzoic acid (2S,3R,4S,6R)-2-{(3R,5R,6R,7R,9R,11R,12R,13S,14R)-7-[(E)-3-(4-chloro-phenyl)-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 (1053248-32-0)

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: Pd(OAc)2; Ph₃P; Et₃N / acetonitrile / 12.5 h / 60 - 80 °C

With hydrogenchloride; palladium diacetate; N-chloro-succinimide; dimethylsulfide; triethylamine; triphenylphosphine; In ethanol; dichloromethane; acetonitrile; 3: Corey-Kim oxidation / 4: Heck coupling;

DOI:10.1021/jm0102349

upstream raw materials:

1-Chloro-4-iodobenzene

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

benzoic acid anhydride

6-O-allylerythromycin A

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