2-Allyl-6-methoxy-benzoic acid (1S,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(E)-4-(4-methoxy-benzyloxy)-but-2-enyl]-4-methyl-hept-6-enyl ester

Base Information

• Chemical Name: 2-Allyl-6-methoxy-benzoic acid (1S,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(E)-4-(4-methoxy-benzyloxy)-but-2-enyl]-4-methyl-hept-6-enyl ester
• CAS No.: 474254-52-9
• Molecular Formula: C₃₇H₅₄O₆Si
• Molecular Weight: 622.918

Synonyms:2-Allyl-6-methoxy-benzoic acid (1S,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(E)-4-(4-methoxy-benzyloxy)-but-2-enyl]-4-methyl-hept-6-enyl ester

Chemical Property of 2-Allyl-6-methoxy-benzoic acid (1S,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(E)-4-(4-methoxy-benzyloxy)-but-2-enyl]-4-methyl-hept-6-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Allyl-6-methoxy-benzoic acid (1S,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(E)-4-(4-methoxy-benzyloxy)-but-2-enyl]-4-methyl-hept-6-enyl ester

There total 11 articles about 2-Allyl-6-methoxy-benzoic acid (1S,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(E)-4-(4-methoxy-benzyloxy)-but-2-enyl]-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: 84.0%

2-allyl-6-methoxy-benzoic acid (325172-28-9) + (E)-(5R,7R,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-8-methyl-undeca-2,10-dien-5-ol (474254-53-0) → 2-Allyl-6-methoxy-benzoic acid (1S,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(E)-4-(4-methoxy-benzyloxy)-but-2-enyl]-4-methyl-hept-6-enyl ester (474254-52-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In benzene; for 24h;

DOI:10.1016/S0040-4020(02)00657-9

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 2-Allyl-6-methoxy-benzoic acid (1S,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(E)-4-(4-methoxy-benzyloxy)-but-2-enyl]-4-methyl-hept-6-enyl ester (474254-52-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 20 °C

2.1: 9-BBN / tetrahydrofuran / 3 h / Heating

2.2: 89 percent / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 0 - 20 °C

3.1: 96 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / -78 - 20 °C

4.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

4.2: 81 percent / tetrahydrofuran / -78 - 20 °C

5.1: 90 percent / aqueous trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 81 percent / NaH; tosylimidazole / tetrahydrofuran / -78 - 0 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7.2: magnesium; 1,2-dibromoethane / various solvents / 0.75 h / -78 °C

7.3: 94 percent / CuI / various solvents / -78 - 0 °C

8.1: 84 percent / triphenylphosphine; diethyl azodicarboxylate / benzene / 24 h

With 2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; sodium hexamethyldisilazane; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; N-tosylimidazole; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; benzene; 3.1: Swern oxidation / 4.2: Wittig methylenation / 6.1: Kishi epoxidation / 8.1: Mitsunobu esterification;

DOI:10.1016/S0040-4020(02)00657-9

Reference yield:

N,N-Diethyl-2-allyl-6-methoxybenzamide (88440-84-0) → 2-Allyl-6-methoxy-benzoic acid (1S,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(E)-4-(4-methoxy-benzyloxy)-but-2-enyl]-4-methyl-hept-6-enyl ester (474254-52-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / I₂ / tetrahydrofuran; H₂O / 24 h / 20 °C

2: 73 percent / zinc; acetic acid / 24 h / 90 °C

3: 84 percent / triphenylphosphine; diethyl azodicarboxylate / benzene / 24 h

With iodine; acetic acid; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; water; benzene; 3: Mitsunobu esterification;

DOI:10.1016/S0040-4020(02)00657-9

upstream raw materials:

2-allyl-6-methoxy-benzoic acid

(E)-(5R,7R,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-8-methyl-undeca-2,10-dien-5-ol

t-butyldimethylsiyl triflate

N,N-Diethyl-2-allyl-6-methoxybenzamide

Downstream raw materials:

(-)-salicylihalamide A

(E)-(7S,9R,10S)-9-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-7-[(E)-4-(4-methoxy-benzyloxy)-but-2-enyl]-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclododecen-5-one

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