(3R,4S)-3-(4-methoxybenzyloxy)-4-methylhex-5-enoic acid

Base Information

Chemical Name:(3R,4S)-3-(4-methoxybenzyloxy)-4-methylhex-5-enoic acid
CAS No.:412909-38-7
Molecular Formula:C₁₅H₂₀O₄
Molecular Weight:264.321
Hs Code.:

Synonyms:(3R,4S)-3-(4-methoxybenzyloxy)-4-methylhex-5-enoic acid

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Chemical Property of (3R,4S)-3-(4-methoxybenzyloxy)-4-methylhex-5-enoic acid

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Technology Process of (3R,4S)-3-(4-methoxybenzyloxy)-4-methylhex-5-enoic acid

There total 22 articles about (3R,4S)-3-(4-methoxybenzyloxy)-4-methylhex-5-enoic acid 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: 88.0%

: 259656-95-6
(3R,4S)-3-(4-methoxybenzyloxy)-4-methyl-5-hexen-1-ol

: 412909-38-7
(3R,4S)-3-(4-methoxybenzyloxy)-4-methylhex-5-enoic acid

Guidance literature:: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In dichloromethane; water; for 48h;
DOI:10.1002/ejoc.201500527

Reference yield:

: 412908-67-9
(3R,4S)-5-(tert-butyldiphenylsilyloxy)-4-methylpent-1-en-3-ol

: 412909-38-7
(3R,4S)-3-(4-methoxybenzyloxy)-4-methylhex-5-enoic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: BF₃*Et₂O / cyclohexane; CH₂Cl₂ / 0 °C

2.1: 9-BBN / tetrahydrofuran / 65 °C

2.2: 30 percent H₂O₂; 15 percent NaOH / 0 °C

3.1: Et₃N / CH₂Cl₂ / 20 °C

4.1: TBAF / tetrahydrofuran / 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

6.1: tetrahydrofuran / -78 - 0 °C

7.1: PPTS / methanol; tetrahydrofuran

8.1: Jones reagent / acetone / 0 °C

With 9-borabicyclo[3.3.1]nonane dimer; jones reagent; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; Dess-Martin periodane; triethylamine; boron trifluoride diethyl etherate; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; acetone; 6.1: Wittig olefination;
DOI:10.1016/S0040-4039(01)02078-0

Reference yield:

: (S)-3-methyl-1-[(R)-p-tolylsulfinyl]but-3-en-2-ol

: 412909-38-7
(3R,4S)-3-(4-methoxybenzyloxy)-4-methylhex-5-enoic acid

Guidance literature:: Multi-step reaction with 12 steps

1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6.17 h / 0 - 20 °C / Inert atmosphere

1.2: 3 h / 0 - 20 °C

2.1: 1H-imidazole; sodium sulfate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

3.1: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

4.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 0.42 h / 0 °C / Inert atmosphere

4.2: 2 h / 20 °C

5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

5.2: 2 h / 0 - 20 °C / Inert atmosphere

6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 19 h / 0 - 20 °C / Inert atmosphere

6.2: 4 h / 0 - 20 °C

6.3: 2 h / 20 °C

7.1: sodium sulfate / dichloromethane / 3 h / 20 °C

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

9.1: N-ethyl-N,N-diisopropylamine; dimethyl sulfoxide; sulfur trioxide pyridine complex / dichloromethane / 2 h / 0 °C / Inert atmosphere

10.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.42 h / 0 °C / Inert atmosphere

10.2: 2.5 h / 0 - 20 °C / Inert atmosphere

11.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / 0 °C / Inert atmosphere

12.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 48 h

With 1H-imidazole; dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; sodium sulfate; triethylamine; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; 4.1: |Pummerer Sulfoxide Rearrangement / 5.2: |Wittig Olefination / 10.2: |Wittig Olefination;
DOI:10.1002/ejoc.201500527