2-Allyl-6-methoxy-benzoic acid (1R,3S,4R)-1-(3-benzyloxy-propyl)-3-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hept-6-enyl ester

Base Information

• Chemical Name: 2-Allyl-6-methoxy-benzoic acid (1R,3S,4R)-1-(3-benzyloxy-propyl)-3-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hept-6-enyl ester
• CAS No.: 345319-61-1
• Molecular Formula: C₄₅H₅₆O₅Si
• Molecular Weight: 705.022

Synonyms:2-Allyl-6-methoxy-benzoic acid (1R,3S,4R)-1-(3-benzyloxy-propyl)-3-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hept-6-enyl ester

Chemical Property of 2-Allyl-6-methoxy-benzoic acid (1R,3S,4R)-1-(3-benzyloxy-propyl)-3-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hept-6-enyl ester

Chemical Property:

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Technology Process of 2-Allyl-6-methoxy-benzoic acid (1R,3S,4R)-1-(3-benzyloxy-propyl)-3-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hept-6-enyl ester

There total 12 articles about 2-Allyl-6-methoxy-benzoic acid (1R,3S,4R)-1-(3-benzyloxy-propyl)-3-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hept-6-enyl 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: 73.0%

2-allyl-6-methoxy-benzoic acid (325172-28-9) + (4S,6S,7R)-1-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-7-methyl-dec-9-en-4-ol (345319-60-0) → 2-Allyl-6-methoxy-benzoic acid (1R,3S,4R)-1-(3-benzyloxy-propyl)-3-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hept-6-enyl ester (345319-61-1)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In diethyl ether; at 0 - 20 ℃; for 1h;

DOI:10.1016/S0040-4039(01)00278-7

Reference yield:

((2S,3S)-3-(3-(benzyloxy)propyl)oxiran-2-yl)methanol (83458-92-8) → 2-Allyl-6-methoxy-benzoic acid (1R,3S,4R)-1-(3-benzyloxy-propyl)-3-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hept-6-enyl ester (345319-61-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: NaAl(OMe)3H / tetrahydrofuran / 0 - 20 °C

2.1: TMSCl / methanol; tetrahydrofuran / 16 h / 20 °C

3.1: DIBAL-H / CH₂Cl₂ / 1 h / 0 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

5.1: toluene / 8 h / -78 °C

6.1: imidazole / dimethylformamide / 16 h / 100 °C

7.1: 9-BBN / tetrahydrofuran / 0.5 h / 20 °C

7.2: NaBO₃ / 16 h / 20 °C

8.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

9.1: tetrahydrofuran / 1 h / -78 - 20 °C

10.1: DDQ / CH₂Cl₂; H₂O / 0.5 h / 20 °C

11.1: 73 percent / DEAD; PPh₃ / diethyl ether / 1 h / 0 - 20 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; chloro-trimethyl-silane; NaAl(OMe)3H; diisobutylaluminium hydride; Dess-Martin periodane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; 4.1: Dess-Martin oxidation / 8.1: Dess-Martin oxidation / 11.1: Mitsunobu esterification;

DOI:10.1016/S0040-4039(01)00278-7

Reference yield:

(3S)-6-(Benzyloxy)hexane-1,3-diol (83458-93-9) → 2-Allyl-6-methoxy-benzoic acid (1R,3S,4R)-1-(3-benzyloxy-propyl)-3-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hept-6-enyl ester (345319-61-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: TMSCl / methanol; tetrahydrofuran / 16 h / 20 °C

2.1: DIBAL-H / CH₂Cl₂ / 1 h / 0 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4.1: toluene / 8 h / -78 °C

5.1: imidazole / dimethylformamide / 16 h / 100 °C

6.1: 9-BBN / tetrahydrofuran / 0.5 h / 20 °C

6.2: NaBO₃ / 16 h / 20 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

8.1: tetrahydrofuran / 1 h / -78 - 20 °C

9.1: DDQ / CH₂Cl₂; H₂O / 0.5 h / 20 °C

10.1: 73 percent / DEAD; PPh₃ / diethyl ether / 1 h / 0 - 20 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; chloro-trimethyl-silane; diisobutylaluminium hydride; Dess-Martin periodane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; 3.1: Dess-Martin oxidation / 7.1: Dess-Martin oxidation / 10.1: Mitsunobu esterification;

DOI:10.1016/S0040-4039(01)00278-7

upstream raw materials:

2-allyl-6-methoxy-benzoic acid

(4S,6S,7R)-1-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-7-methyl-dec-9-en-4-ol

((2S,3S)-3-(3-(benzyloxy)propyl)oxiran-2-yl)methanol

(3S)-6-(Benzyloxy)hexane-1,3-diol

Downstream raw materials:

(E)-(7R,9S,10R)-7-(3-Benzyloxy-propyl)-9-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclododecen-5-one

ent-salicylihalamide B

(+)-Salicylihalamide A

(E)-(7R,9S,10R)-9-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxy-7-(3-hydroxy-propyl)-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclododecen-5-one

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