(1R,2S,3S,4S)-2-(3R-butenyl)-4-[4-methoxy-benzyloxy]-3-methyl-cyclopentanol

Base Information

• Chemical Name: (1R,2S,3S,4S)-2-(3R-butenyl)-4-[4-methoxy-benzyloxy]-3-methyl-cyclopentanol
• CAS No.: 286408-56-8
• Molecular Formula: C₁₈H₂₆O₃
• Molecular Weight: 290.403
• Mol file: 286408-56-8.mol

Synonyms:(1R,2S,3S,4S)-2-(3R-butenyl)-4-[4-methoxy-benzyloxy]-3-methyl-cyclopentanol

Chemical Property of (1R,2S,3S,4S)-2-(3R-butenyl)-4-[4-methoxy-benzyloxy]-3-methyl-cyclopentanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3S,4S)-2-(3R-butenyl)-4-[4-methoxy-benzyloxy]-3-methyl-cyclopentanol

There total 10 articles about (1R,2S,3S,4S)-2-(3R-butenyl)-4-[4-methoxy-benzyloxy]-3-methyl-cyclopentanol 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: 82.0%

methyllithium (917-54-4) + Methyltriphenylphosphonium bromide (1779-49-3) + (1R,3RS,4S,5R,6S,7S)-4,6-dimethyl-7-[4-methoxy-benzyloxy]-2-oxabicyclo[3.3.0]-octane-3-ol (286408-55-7) → (1R,2S,3S,4S)-2-(3R-butenyl)-4-[4-methoxy-benzyloxy]-3-methyl-cyclopentanol (286408-56-8)

Guidance literature:

methyllithium; Methyltriphenylphosphonium bromide; In tetrahydrofuran; diethyl ether; at 25 ℃; for 0.5h;

(1R,3RS,4S,5R,6S,7S)-4,6-dimethyl-7-[4-methoxy-benzyloxy]-2-oxabicyclo[3.3.0]-octane-3-ol; In tetrahydrofuran; diethyl ether; at 50 ℃; for 12h; Further stages.;

DOI:10.1021/ol006003y

Reference yield:

(1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one (34638-25-0,38110-77-9,43119-28-4,54483-22-6,26054-46-6) → (1R,2S,3S,4S)-2-(3R-butenyl)-4-[4-methoxy-benzyloxy]-3-methyl-cyclopentanol (286408-56-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: LHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: 86 percent / tetrahydrofuran / 1 h / -60 °C

2.1: LHMDS / tetrahydrofuran / 2 h / -78 °C

2.2: 78 percent / NH₄Cl / H₂O; tetrahydrofuran; diethyl ether

3.1: AcOOH; NaOAc / acetic acid / 48 h / 20 °C

4.1: 91 percent / DIBAL-H / toluene; CH₂Cl₂ / 3 h / -78 °C

5.1: 67 percent / Dowex-50 / 4 h / 20 °C

6.1: CuI / diethyl ether / 0.25 h / -78 - -20 °C

6.2: diethyl ether / 5 h / -30 °C

7.1: NaH; n-Bu₄NI / dimethylformamide; tetrahydrofuran / 0.67 h / 0 °C

7.2: 90 percent / dimethylformamide; tetrahydrofuran / 40 h / 20 °C

8.1: 98 percent / HCl / tetrahydrofuran; H₂O / 2 h / 40 °C

9.1: tetrahydrofuran; diethyl ether / 0.5 h / 25 °C

9.2: 82 percent / tetrahydrofuran; diethyl ether / 12 h / 50 °C

With hydrogenchloride; peracetic acid; copper(l) iodide; Dowex-50; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; 1.1: Metallation / 1.2: Methylation / 2.1: Metallation / 2.2: Protonation / 3.1: Epoxidation / 4.1: Reduction / 5.1: Etherification / 6.1: Addition / 6.2: Ring cleavage / 7.1: Reduction / 7.2: Addition / 8.1: Hydrolysis / 9.1: Addition / 9.2: Ring cleavage;

DOI:10.1021/ol006003y

Reference yield:

(+)-(1R,4R,5R)-4-methyl-2-oxabicyclo<3.3.0>oct-6-en-3-one (137567-91-0) → (1R,2S,3S,4S)-2-(3R-butenyl)-4-[4-methoxy-benzyloxy]-3-methyl-cyclopentanol (286408-56-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: LHMDS / tetrahydrofuran / 2 h / -78 °C

1.2: 78 percent / NH₄Cl / H₂O; tetrahydrofuran; diethyl ether

2.1: AcOOH; NaOAc / acetic acid / 48 h / 20 °C

3.1: 91 percent / DIBAL-H / toluene; CH₂Cl₂ / 3 h / -78 °C

4.1: 67 percent / Dowex-50 / 4 h / 20 °C

5.1: CuI / diethyl ether / 0.25 h / -78 - -20 °C

5.2: diethyl ether / 5 h / -30 °C

6.1: NaH; n-Bu₄NI / dimethylformamide; tetrahydrofuran / 0.67 h / 0 °C

6.2: 90 percent / dimethylformamide; tetrahydrofuran / 40 h / 20 °C

7.1: 98 percent / HCl / tetrahydrofuran; H₂O / 2 h / 40 °C

8.1: tetrahydrofuran; diethyl ether / 0.5 h / 25 °C

8.2: 82 percent / tetrahydrofuran; diethyl ether / 12 h / 50 °C

With hydrogenchloride; peracetic acid; copper(l) iodide; Dowex-50; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; 1.1: Metallation / 1.2: Protonation / 2.1: Epoxidation / 3.1: Reduction / 4.1: Etherification / 5.1: Addition / 5.2: Ring cleavage / 6.1: Reduction / 6.2: Addition / 7.1: Hydrolysis / 8.1: Addition / 8.2: Ring cleavage;

DOI:10.1021/ol006003y

upstream raw materials:

methyllithium

Methyltriphenylphosphonium bromide

(1R,3RS,4S,5R,6S,7S)-4,6-dimethyl-7-[4-methoxy-benzyloxy]-2-oxabicyclo[3.3.0]-octane-3-ol

(1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one

Downstream raw materials:

(3S,4R,5S)-6-(3R-butenyl)-4-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-one

(2S,3S,4S)-2-(3R-butenyl)-3-methyl-4-[4-methoxy-benzyloxy]-cyclopentanone