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

Base Information

• Chemical Name: (1S,2S,4R,5R)-2-benzoyloxy-4-(2-methoxyethoxymethoxymethyl)-8-methylbicyclo<3.3.0>oct-7-ene
• CAS No.: 110943-04-9
• Molecular Formula: C₂₁H₂₈O₅
• Molecular Weight: 360.45

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

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

Chemical Property:

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

There total 5 articles about (1S,2S,4R,5R)-2-benzoyloxy-4-(2-methoxyethoxymethoxymethyl)-8-methylbicyclo<3.3.0>oct-7-ene 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: 80.0%

benzoyl chloride (98-88-4) + (1S,2S,4R,5R)-4-(2-methoxyethoxymethoxymethyl)-8-methylbicyclo<3.3.0>oct-7-en-2-ol (110943-03-8) → (1S,2S,4R,5R)-2-benzoyloxy-4-(2-methoxyethoxymethoxymethyl)-8-methylbicyclo<3.3.0>oct-7-ene (110943-04-9)

Guidance literature:

With pyridine; In dichloromethane; for 6h; Ambient temperature;

DOI:10.1248/cpb.34.4629

Reference yield:

(1S,4R,5R)-4-hydroxymethyl-8-methylbicyclo<3.3.0>oct-7-en-2-one (110943-02-7) → (1S,2S,4R,5R)-2-benzoyloxy-4-(2-methoxyethoxymethoxymethyl)-8-methylbicyclo<3.3.0>oct-7-ene (110943-04-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 2 h / 30 °C

2: 79 percent / NaBH₄ / methanol / 0.5 h / -10 °C

3: 80 percent / pyridine / CH₂Cl₂ / 6 h / Ambient temperature

With pyridine; sodium tetrahydroborate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1248/cpb.34.4629

Reference yield:

(1S,4R,5R)-4-acetoxymethyl-8-methylbicyclo<3.3.0>oct-7-en-2-one (110943-01-6) → (1S,2S,4R,5R)-2-benzoyloxy-4-(2-methoxyethoxymethoxymethyl)-8-methylbicyclo<3.3.0>oct-7-ene (110943-04-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 58 percent / K₂CO₃ / methanol / 3.5 h / Ambient temperature

2: 95 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 2 h / 30 °C

3: 79 percent / NaBH₄ / methanol / 0.5 h / -10 °C

4: 80 percent / pyridine / CH₂Cl₂ / 6 h / Ambient temperature

With pyridine; sodium tetrahydroborate; potassium carbonate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1248/cpb.34.4629

upstream raw materials:

benzoyl chloride

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

(1S,4R,5R)-4-hydroxymethyl-8-methylbicyclo<3.3.0>oct-7-en-2-one

(1S,4R,5R)-4-acetoxymethyl-8-methylbicyclo<3.3.0>oct-7-en-2-one

Downstream raw materials:

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

Benzoic acid (3R,4R)-2-acetyl-4-(2-methoxy-ethoxymethoxymethyl)-3-(2-oxo-ethyl)-cyclopentyl ester

<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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