2-allyl-6-methoxy-benzoic acid (1S,3R,4S)-1-[2-(4-methoxybenzyl)-ethyl]-3-methoxymethyl-4,7-dimethyl-oct-6-enyl ester

Base Information

• Chemical Name: 2-allyl-6-methoxy-benzoic acid (1S,3R,4S)-1-[2-(4-methoxybenzyl)-ethyl]-3-methoxymethyl-4,7-dimethyl-oct-6-enyl ester
• CAS No.: 405872-68-6
• Molecular Formula: C₃₃H₄₆O₇
• Molecular Weight: 554.724
• Mol file: 405872-68-6.mol

Synonyms:2-allyl-6-methoxy-benzoic acid (1S,3R,4S)-1-[2-(4-methoxybenzyl)-ethyl]-3-methoxymethyl-4,7-dimethyl-oct-6-enyl ester

Chemical Property of 2-allyl-6-methoxy-benzoic acid (1S,3R,4S)-1-[2-(4-methoxybenzyl)-ethyl]-3-methoxymethyl-4,7-dimethyl-oct-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)-1-[2-(4-methoxybenzyl)-ethyl]-3-methoxymethyl-4,7-dimethyl-oct-6-enyl ester

There total 11 articles about 2-allyl-6-methoxy-benzoic acid (1S,3R,4S)-1-[2-(4-methoxybenzyl)-ethyl]-3-methoxymethyl-4,7-dimethyl-oct-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: 93.0%

2-allyl-6-methoxy-benzoic acid (325172-28-9) + (3R,5R,6S)-1-(4-methoxybenzyl)-5-methoxymethyl-6,9-dimethyl-dec-8-en-3-ol (405872-46-0) → 2-allyl-6-methoxy-benzoic acid (1S,3R,4S)-1-[2-(4-methoxybenzyl)-ethyl]-3-methoxymethyl-4,7-dimethyl-oct-6-enyl ester (405872-68-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In diethyl ether; for 20h;

DOI:10.1002/1521-3765(20011217)7:24<5286::AID-CHEM5286>3.0.CO;2-G

Reference yield:

(S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-2,5-dimethyl-hex-4-en-1-one (127392-87-4) → 2-allyl-6-methoxy-benzoic acid (1S,3R,4S)-1-[2-(4-methoxybenzyl)-ethyl]-3-methoxymethyl-4,7-dimethyl-oct-6-enyl ester (405872-68-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 95 percent / aq. H₂O₂; LiOH*H₂O / tetrahydrofuran / 25 h / 0 - 20 °C

2.1: (CH₃)2CH=CH(Cl)NMe₂ / CH₂Cl₂ / 1.5 h

3.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

3.2: 81 percent / hexane; tetrahydrofuran / 2 h / 20 °C

4.1: 94 percent / H₂ / [((S)-BINAP)RuCl₂]2*NEt₃ / methanol; tetrahydrofuran / 4 h / 80 °C / 3040.2 Torr

5.1: 89 percent / DMAP; i-Pr₂NEt / CH₂Cl₂ / 40 h / 20 °C

6.1: LiHMDS / tetrahydrofuran / 1.5 h / -45 - -30 °C

6.2: 95 percent / tetrahydrofuran / 3 h / -40 - -30 °C

7.1: 93 percent / H₂ / [((S)-BINAP)RuCl₂]2*NEt₃ / methanol; tetrahydrofuran / 6.5 h / 25 °C / 60804.1 Torr

8.1: 90 percent / LiAlH₄ / diethyl ether / 6 h / 0 °C

9.1: NaH / dimethylformamide / 1.25 h

9.2: 76 percent / dimethylformamide / 1.5 h

10.1: 93 percent / PPh₃; DEAD / diethyl ether / 20 h

With dmap; lithium hydroxide; lithium aluminium tetrahydride; (CH₃)2CH=CH(Cl)NMe₂; hydrogen; dihydrogen peroxide; sodium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; lithium diisopropyl amide; diethylazodicarboxylate; RuCl₂[(S)-BINAP]; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 10.1: Mitsunobu reaction;

DOI:10.1002/1521-3765(20011217)7:24<5286::AID-CHEM5286>3.0.CO;2-G

Reference yield:

prenyl bromide (870-63-3) → 2-allyl-6-methoxy-benzoic acid (1S,3R,4S)-1-[2-(4-methoxybenzyl)-ethyl]-3-methoxymethyl-4,7-dimethyl-oct-6-enyl ester (405872-68-6)

Guidance literature:

Multi-step reaction with 11 steps

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

1.2: 79 percent / HMPA / hexane; tetrahydrofuran / -78 - 20 °C

2.1: 95 percent / aq. H₂O₂; LiOH*H₂O / tetrahydrofuran / 25 h / 0 - 20 °C

3.1: (CH₃)2CH=CH(Cl)NMe₂ / CH₂Cl₂ / 1.5 h

4.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

4.2: 81 percent / hexane; tetrahydrofuran / 2 h / 20 °C

5.1: 94 percent / H₂ / [((S)-BINAP)RuCl₂]2*NEt₃ / methanol; tetrahydrofuran / 4 h / 80 °C / 3040.2 Torr

6.1: 89 percent / DMAP; i-Pr₂NEt / CH₂Cl₂ / 40 h / 20 °C

7.1: LiHMDS / tetrahydrofuran / 1.5 h / -45 - -30 °C

7.2: 95 percent / tetrahydrofuran / 3 h / -40 - -30 °C

8.1: 93 percent / H₂ / [((S)-BINAP)RuCl₂]2*NEt₃ / methanol; tetrahydrofuran / 6.5 h / 25 °C / 60804.1 Torr

9.1: 90 percent / LiAlH₄ / diethyl ether / 6 h / 0 °C

10.1: NaH / dimethylformamide / 1.25 h

10.2: 76 percent / dimethylformamide / 1.5 h

11.1: 93 percent / PPh₃; DEAD / diethyl ether / 20 h

With dmap; lithium hydroxide; lithium aluminium tetrahydride; n-butyllithium; (CH₃)2CH=CH(Cl)NMe₂; N-cyclohexylisopropylamine; hydrogen; dihydrogen peroxide; sodium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; lithium diisopropyl amide; diethylazodicarboxylate; RuCl₂[(S)-BINAP]; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 11.1: Mitsunobu reaction;

DOI:10.1002/1521-3765(20011217)7:24<5286::AID-CHEM5286>3.0.CO;2-G

upstream raw materials:

2-allyl-6-methoxy-benzoic acid

(3R,5R,6S)-1-(4-methoxybenzyl)-5-methoxymethyl-6,9-dimethyl-dec-8-en-3-ol

(S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,5-dimethyl-hex-4-en-1-one

prenyl bromide

Downstream raw materials:

salicylihalamide B

(-)-salicylihalamide A

(3S,5R,6S,Z)-14-methoxy-3-(2-((4-methoxybenzyl)oxy)-ethyl)-5-(methoxymethoxy)-6-methyl-3,4,5,6,7,10-hexahydro-1H-benzo[c][1]oxacyclododecin-1-one

(3S,5R,6S,E)-14-methoxy-3-(2-((4-methoxybenzyl)oxy)-ethyl)-5-(methoxymethoxy)-6-methyl-3,4,5,6,7,10-hexahydro-1H-benzo[c][1]oxacyclododecin-1-one