(1R,2R)-3-acetyl-2-formylmethyl-1-(2-methoxyethoxymethoxymethyl)-3-cyclopentene

Base Information

• Chemical Name: (1R,2R)-3-acetyl-2-formylmethyl-1-(2-methoxyethoxymethoxymethyl)-3-cyclopentene
• CAS No.: 110943-06-1
• Molecular Formula: C₁₄H₂₂O₅
• Molecular Weight: 270.326

Synonyms:(1R,2R)-3-acetyl-2-formylmethyl-1-(2-methoxyethoxymethoxymethyl)-3-cyclopentene

Chemical Property of (1R,2R)-3-acetyl-2-formylmethyl-1-(2-methoxyethoxymethoxymethyl)-3-cyclopentene

Chemical Property:

Purity/Quality:

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Technology Process of (1R,2R)-3-acetyl-2-formylmethyl-1-(2-methoxyethoxymethoxymethyl)-3-cyclopentene

There total 1 articles about (1R,2R)-3-acetyl-2-formylmethyl-1-(2-methoxyethoxymethoxymethyl)-3-cyclopentene 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:

(1S,2S,4R,5R)-2-benzoyloxy-4-(2-methoxyethoxymethoxymethyl)-8-methylbicyclo<3.3.0>oct-7-ene (110943-04-9) → (1R,2R)-3-acetyl-2-formylmethyl-1-(2-methoxyethoxymethoxymethyl)-3-cyclopentene (110943-06-1) + Benzoic acid (3R,4R)-2-acetyl-4-(2-methoxy-ethoxymethoxymethyl)-3-(2-oxo-ethyl)-cyclopentyl ester (110943-05-0)

Guidance literature:

With ozone; zinc; Multistep reaction. Title compound not separated from byproducts; 1.) dichloromethane, -78 deg C; 2.) AcOH, 10-20 deg C;

DOI:10.1248/cpb.34.4629

Reference yield:

(1R,2R)-3-acetyl-2-formylmethyl-1-(2-methoxyethoxymethoxymethyl)-3-cyclopentene (110943-06-1) → (1S,5R,6S)-6-hydroxymethyl-3-oxo-2-oxabicyclo<3.3.0>octane (36969-85-4,43119-34-2,61473-95-8,71116-15-9,111056-88-3,136780-61-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 79 percent / Jones reagent / acetone / 0.5 h / -10 °C

2: 87 percent / 5percent Pd/C / methanol / Ambient temperature

3: 96 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

4: 78 percent / 80percent MCPBA, NaHCO₃ / CH₂Cl₂ / 5 h / Ambient temperature

5: KOH / methanol; H₂O / 2 h / Ambient temperature

6: 1.) triphenylphosphine, DEAD; 2.) TiCl₄ / 1.) benzene, 5-10 deg C, 3 h; 2.) methylene dichloride, 0 deg C, 1 h

7: 50 percent / 1.) DMSO, oxalyl chloride; 2.) triethylamine / CH₂Cl₂ / -60 °C / 1.) 15 min; 2.) 0.5 h

8: 15 mg / NaBH₄ / methanol / 0.5 h / 0 °C

With potassium hydroxide; sodium tetrahydroborate; jones reagent; oxalyl dichloride; titanium tetrachloride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In methanol; dichloromethane; water; acetone;

DOI:10.1248/cpb.34.4629

Reference yield:

(1R,2R)-3-acetyl-2-formylmethyl-1-(2-methoxyethoxymethoxymethyl)-3-cyclopentene (110943-06-1) → <3aα,4α6aα>-hexahydro-2-oxo-2H-cyclopenta furan-4-carboxaldehyde (201421-82-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 79 percent / Jones reagent / acetone / 0.5 h / -10 °C

2: 87 percent / 5percent Pd/C / methanol / Ambient temperature

3: 96 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

4: 78 percent / 80percent MCPBA, NaHCO₃ / CH₂Cl₂ / 5 h / Ambient temperature

5: KOH / methanol; H₂O / 2 h / Ambient temperature

6: 1.) triphenylphosphine, DEAD; 2.) TiCl₄ / 1.) benzene, 5-10 deg C, 3 h; 2.) methylene dichloride, 0 deg C, 1 h

7: 50 percent / 1.) DMSO, oxalyl chloride; 2.) triethylamine / CH₂Cl₂ / -60 °C / 1.) 15 min; 2.) 0.5 h

With potassium hydroxide; jones reagent; oxalyl dichloride; titanium tetrachloride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In methanol; dichloromethane; water; acetone;

DOI:10.1248/cpb.34.4629

upstream raw materials:

(1S,2S,4R,5R)-2-benzoyloxy-4-(2-methoxyethoxymethoxymethyl)-8-methylbicyclo<3.3.0>oct-7-ene

Downstream raw materials:

<3aα,4α6aα>-hexahydro-2-oxo-2H-cyclopenta furan-4-carboxaldehyde

(1S,5R,6S)-6-hydroxymethyl-3-oxo-2-oxabicyclo<3.3.0>octane

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