benzoic acid 5-azido-6-methyl-4-(3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-2-[1,6,12-tris-benzyloxy-9-chloro-8,11-dimethoxy-2-(1-methoxycarbonyl-ethylcarbamoyl)-3-methyl-5,6-dihydro-benzo[a]anthracen-5-yloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: benzoic acid 5-azido-6-methyl-4-(3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-2-[1,6,12-tris-benzyloxy-9-chloro-8,11-dimethoxy-2-(1-methoxycarbonyl-ethylcarbamoyl)-3-methyl-5,6-dihydro-benzo[a]anthracen-5-yloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 863423-85-2
• Molecular Formula: C₇₁H₇₁ClN₄O₂₀
• Molecular Weight: 1335.81

Synonyms:benzoic acid 5-azido-6-methyl-4-(3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-2-[1,6,12-tris-benzyloxy-9-chloro-8,11-dimethoxy-2-(1-methoxycarbonyl-ethylcarbamoyl)-3-methyl-5,6-dihydro-benzo[a]anthracen-5-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property of benzoic acid 5-azido-6-methyl-4-(3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-2-[1,6,12-tris-benzyloxy-9-chloro-8,11-dimethoxy-2-(1-methoxycarbonyl-ethylcarbamoyl)-3-methyl-5,6-dihydro-benzo[a]anthracen-5-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of benzoic acid 5-azido-6-methyl-4-(3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-2-[1,6,12-tris-benzyloxy-9-chloro-8,11-dimethoxy-2-(1-methoxycarbonyl-ethylcarbamoyl)-3-methyl-5,6-dihydro-benzo[a]anthracen-5-yloxy]-tetrahydro-pyran-3-yl ester

There total 15 articles about benzoic acid 5-azido-6-methyl-4-(3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-2-[1,6,12-tris-benzyloxy-9-chloro-8,11-dimethoxy-2-(1-methoxycarbonyl-ethylcarbamoyl)-3-methyl-5,6-dihydro-benzo[a]anthracen-5-yloxy]-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:

7-chloro-5,8-dimethoxy-4-methoxymethoxy-2-naphthoic acid (863423-73-8) → benzoic acid 5-azido-6-methyl-4-(3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-2-[1,6,12-tris-benzyloxy-9-chloro-8,11-dimethoxy-2-(1-methoxycarbonyl-ethylcarbamoyl)-3-methyl-5,6-dihydro-benzo[a]anthracen-5-yloxy]-tetrahydro-pyran-3-yl ester (863423-85-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 99 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; 4-(dimethylamino)pyridine / toluene / 0.33 h / 20 °C

2.1: 96 percent / CF₃COOH / CH₂Cl₂ / 4 h / 25 °C

3.1: 60 percent / PPh₃; tBuCO₂Na / Pd(OAc)2 / N,N-dimethyl-acetamide / 60 h / 110 °C

4.1: CH₂Cl₂ / 43 h / 0 °C

5.1: 97 percent / Cs₂CO₃ / dimethylformamide / 1.17 h / 0 - 20 °C

6.1: 100 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 0.33 h / 0 °C

7.1: 2.6-di-tert-butylpyridine / CH₂Cl₂ / 1 h / 20 °C

8.1: L-Selectride / 0.33 h / 0 °C

8.2: 96 percent / silica gel / 17 h / 20 °C

9.1: trimethylsilyl trifluoromethanesulfonate / toluene / 6 h / -15 °C

10.1: nBu₄NF / tetrahydrofuran / 1 h / 0 °C

11.1: MnO₂ / CH₂Cl₂ / 16 h / 20 °C

12.1: 95 percent / SmI₂; BF₃*OEt₂; methanol / tetrahydrofuran / 0.18 h / -78 - 0 °C

13.1: NaOH / ethanol / 2 h / 100 °C

14.1: BOP; Et₃N / dimethylformamide / 1 h / 20 °C

15.1: 72 percent / Cp₂HfCl₂; AgOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 11.33 h / -78 - -35 °C

With 1H-imidazole; methanol; dmap; manganese(IV) oxide; sodium hydroxide; 2,6-di-tert-butyl-pyridine; samarium diiodide; bis(cyclopentadienyl)hafnium dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; iodine; silver trifluoromethanesulfonate; L-Selectride; sodium pivalate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium diacetate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; toluene; 1.1: Yamaguchi esterification;

DOI:10.1002/anie.200501210

Reference yield:

methyl 2-hydroxy-3-iodo-6-methyl-4-[(triisopropylsiloxy)methyl]benzoate (863423-74-9) → benzoic acid 5-azido-6-methyl-4-(3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-2-[1,6,12-tris-benzyloxy-9-chloro-8,11-dimethoxy-2-(1-methoxycarbonyl-ethylcarbamoyl)-3-methyl-5,6-dihydro-benzo[a]anthracen-5-yloxy]-tetrahydro-pyran-3-yl ester (863423-85-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 99 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; 4-(dimethylamino)pyridine / toluene / 0.33 h / 20 °C

2.1: 96 percent / CF₃COOH / CH₂Cl₂ / 4 h / 25 °C

3.1: 60 percent / PPh₃; tBuCO₂Na / Pd(OAc)2 / N,N-dimethyl-acetamide / 60 h / 110 °C

4.1: CH₂Cl₂ / 43 h / 0 °C

5.1: 97 percent / Cs₂CO₃ / dimethylformamide / 1.17 h / 0 - 20 °C

6.1: 100 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 0.33 h / 0 °C

7.1: 2.6-di-tert-butylpyridine / CH₂Cl₂ / 1 h / 20 °C

8.1: L-Selectride / 0.33 h / 0 °C

8.2: 96 percent / silica gel / 17 h / 20 °C

9.1: trimethylsilyl trifluoromethanesulfonate / toluene / 6 h / -15 °C

10.1: nBu₄NF / tetrahydrofuran / 1 h / 0 °C

11.1: MnO₂ / CH₂Cl₂ / 16 h / 20 °C

12.1: 95 percent / SmI₂; BF₃*OEt₂; methanol / tetrahydrofuran / 0.18 h / -78 - 0 °C

13.1: NaOH / ethanol / 2 h / 100 °C

14.1: BOP; Et₃N / dimethylformamide / 1 h / 20 °C

15.1: 72 percent / Cp₂HfCl₂; AgOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 11.33 h / -78 - -35 °C

With 1H-imidazole; methanol; dmap; manganese(IV) oxide; sodium hydroxide; 2,6-di-tert-butyl-pyridine; samarium diiodide; bis(cyclopentadienyl)hafnium dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; iodine; silver trifluoromethanesulfonate; L-Selectride; sodium pivalate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium diacetate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; toluene; 1.1: Yamaguchi esterification;

DOI:10.1002/anie.200501210

Reference yield:

2-iodo-6-methoxycarbonyl-5-methyl-3-[(triisopropylsiloxy)methyl]phenyl 7-chloro-4-hydroxy-5,8-dimethoxy-2-naphthoate (863423-89-6) → benzoic acid 5-azido-6-methyl-4-(3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-2-[1,6,12-tris-benzyloxy-9-chloro-8,11-dimethoxy-2-(1-methoxycarbonyl-ethylcarbamoyl)-3-methyl-5,6-dihydro-benzo[a]anthracen-5-yloxy]-tetrahydro-pyran-3-yl ester (863423-85-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 60 percent / PPh₃; tBuCO₂Na / Pd(OAc)2 / N,N-dimethyl-acetamide / 60 h / 110 °C

2.1: CH₂Cl₂ / 43 h / 0 °C

3.1: 97 percent / Cs₂CO₃ / dimethylformamide / 1.17 h / 0 - 20 °C

4.1: 100 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 0.33 h / 0 °C

5.1: 2.6-di-tert-butylpyridine / CH₂Cl₂ / 1 h / 20 °C

6.1: L-Selectride / 0.33 h / 0 °C

6.2: 96 percent / silica gel / 17 h / 20 °C

7.1: trimethylsilyl trifluoromethanesulfonate / toluene / 6 h / -15 °C

8.1: nBu₄NF / tetrahydrofuran / 1 h / 0 °C

9.1: MnO₂ / CH₂Cl₂ / 16 h / 20 °C

10.1: 95 percent / SmI₂; BF₃*OEt₂; methanol / tetrahydrofuran / 0.18 h / -78 - 0 °C

11.1: NaOH / ethanol / 2 h / 100 °C

12.1: BOP; Et₃N / dimethylformamide / 1 h / 20 °C

13.1: 72 percent / Cp₂HfCl₂; AgOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 11.33 h / -78 - -35 °C

With 1H-imidazole; methanol; manganese(IV) oxide; sodium hydroxide; 2,6-di-tert-butyl-pyridine; samarium diiodide; bis(cyclopentadienyl)hafnium dichloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; iodine; silver trifluoromethanesulfonate; L-Selectride; sodium pivalate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate; triethylamine; triphenylphosphine; palladium diacetate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; toluene;

DOI:10.1002/anie.200501210

upstream raw materials:

7-chloro-5,8-dimethoxy-4-methoxymethoxy-2-naphthoic acid

methyl 2-hydroxy-3-iodo-6-methyl-4-[(triisopropylsiloxy)methyl]benzoate

2-iodo-6-methoxycarbonyl-5-methyl-3-[(triisopropylsiloxy)methyl]phenyl 7-chloro-4-hydroxy-5,8-dimethoxy-2-naphthoate

9-chloro-12-hydroxy-8,11-dimethoxy-3-methyl-6-oxo-1-triisopropylsilanyloxymethyl-6H-naphtho[2,3-c]chromene-4-carboxylic acid methyl ester

Downstream raw materials:

C₇₂H₇₅ClN₂O₂₀

C₇₄H₇₀N₄O₂₂

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