(1R,3S,4S,5R,6R,7S)-3-methoxy-4-methyl-2-oxabicyclo[3.3.0]-octane

Base Information

• Chemical Name: (1R,3S,4S,5R,6R,7S)-3-methoxy-4-methyl-2-oxabicyclo[3.3.0]-octane
• CAS No.: 286408-52-4
• Molecular Formula: C₉H₁₄O₃
• Molecular Weight: 170.208
• Mol file: 286408-52-4.mol

Synonyms:(1R,3S,4S,5R,6R,7S)-3-methoxy-4-methyl-2-oxabicyclo[3.3.0]-octane

Chemical Property of (1R,3S,4S,5R,6R,7S)-3-methoxy-4-methyl-2-oxabicyclo[3.3.0]-octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,4S,5R,6R,7S)-3-methoxy-4-methyl-2-oxabicyclo[3.3.0]-octane

There total 1 articles about (1R,3S,4S,5R,6R,7S)-3-methoxy-4-methyl-2-oxabicyclo[3.3.0]-octane 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:

(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,3S,4S,5R,6R,7S)-3-methoxy-4-methyl-2-oxabicyclo[3.3.0]-octane (286408-52-4)

Guidance literature:

Multi-step reaction with 5 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

With peracetic acid; Dowex-50; sodium acetate; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetic acid; toluene; 1.1: Metallation / 1.2: Methylation / 2.1: Metallation / 2.2: Protonation / 3.1: Epoxidation / 4.1: Reduction / 5.1: Etherification;

DOI:10.1021/ol006003y

Reference yield:

(1R,3S,4S,5R,6R,7S)-3-methoxy-4-methyl-2-oxabicyclo[3.3.0]-octane (286408-52-4) → (1R,3RS,4S,5R,6S,7S)-4,6-dimethyl-7-[4-methoxy-benzyloxy]-2-oxabicyclo[3.3.0]-octane-3-ol (286408-55-7)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: diethyl ether / 5 h / -30 °C

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

2.2: 90 percent / dimethylformamide; tetrahydrofuran / 40 h / 20 °C

3.1: 98 percent / HCl / tetrahydrofuran; H₂O / 2 h / 40 °C

With hydrogenchloride; copper(l) iodide; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; 1.1: Addition / 1.2: Ring cleavage / 2.1: Reduction / 2.2: Addition / 3.1: Hydrolysis;

DOI:10.1021/ol006003y

Reference yield:

(1R,3S,4S,5R,6R,7S)-3-methoxy-4-methyl-2-oxabicyclo[3.3.0]-octane (286408-52-4) → (2S,3S,4S)-2-(3R-butenyl)-3-methyl-4-[4-methoxy-benzyloxy]-cyclopentanone (286408-57-9)

Guidance literature:

Multi-step reaction with 5 steps

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

1.2: diethyl ether / 5 h / -30 °C

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

2.2: 90 percent / dimethylformamide; tetrahydrofuran / 40 h / 20 °C

3.1: 98 percent / HCl / tetrahydrofuran; H₂O / 2 h / 40 °C

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

4.2: 82 percent / tetrahydrofuran; diethyl ether / 12 h / 50 °C

5.1: 81 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂ / 12 h / 20 °C

With hydrogenchloride; copper(l) iodide; tetrapropylammonium perruthennate; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Addition / 1.2: Ring cleavage / 2.1: Reduction / 2.2: Addition / 3.1: Hydrolysis / 4.1: Addition / 4.2: Ring cleavage / 5.1: Oxidation;

DOI:10.1021/ol006003y

upstream raw materials:

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

Downstream raw materials:

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

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

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

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