(3aS,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-pentalene-1-carbaldehyde

Base Information

• Chemical Name: (3aS,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-pentalene-1-carbaldehyde
• CAS No.: 75232-24-5
• Molecular Formula: C₁₇H₁₈O₂
• Molecular Weight: 254.329
• Mol file: 75232-24-5.mol

Synonyms:(3aS,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-pentalene-1-carbaldehyde

Chemical Property of (3aS,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-pentalene-1-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-pentalene-1-carbaldehyde

There total 1 articles about (3aS,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-pentalene-1-carbaldehyde 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%

((3aS,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-pentalen-1-yl)-methanol (75232-23-4) → (3aS,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-pentalene-1-carbaldehyde (75232-24-5)

Guidance literature:

With dipyridinium dichromate; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)71385-2

Reference yield: 95.0%

(methoxymethylene)triphenylphosphorane (20763-19-3) + (3aS,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-pentalene-1-carbaldehyde (75232-24-5) → (1S,3aS,6aS)-1-Benzyloxymethyl-4-((E)-2-methoxy-vinyl)-1,3a,6,6a-tetrahydro-pentalene (75232-25-6,75281-65-1)

Guidance literature:

In tetrahydrofuran; dimethyl sulfoxide; at 0 ℃;

DOI:10.1016/S0040-4039(00)71385-2

Reference yield:

(3aS,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-pentalene-1-carbaldehyde (75232-24-5) → (1S,2S,3S,3aS,8aR)-1-Benzyloxymethyl-3-bromo-2-hydroxy-1,2,3,3a,8,8a-hexahydro-cyclopenta[a]indene-6-carboxylic acid methyl ester (75232-27-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / dimethylsulfoxide; tetrahydrofuran / 0 °C

2: toluene / 100 °C

3: 65 percent / SiO₂ / CH₂Cl₂ / Ambient temperature

4: 96 percent / N-bromosuccinimide / H₂O; dimethylsulfoxide

With N-Bromosuccinimide; silica gel; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene;

DOI:10.1016/S0040-4039(00)71385-2

upstream raw materials:

((3aS,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-pentalen-1-yl)-methanol

Downstream raw materials:

(1S,3aS,6aS)-1-Benzyloxymethyl-4-((E)-2-methoxy-vinyl)-1,3a,6,6a-tetrahydro-pentalene

(1S,3aS,6aS)-1-Benzyloxymethyl-4-((Z)-2-methoxy-vinyl)-1,3a,6,6a-tetrahydro-pentalene

(1S,3aS,6aS)-1-Benzyloxymethyl-4-((E)-2-methoxy-vinyl)-1,3a,6,6a-tetrahydro-pentalene

(1S,3aS,8aS)-1-Benzyloxymethyl-1,3a,8,8a-tetrahydro-cyclopenta[a]indene-6-carboxylic acid methyl ester