7-Benzyloxymethyl-2-methylthiobicyclo<2.2.1>hept-5-ene-2-carboxylic Acid

Base Information

• Chemical Name: 7-Benzyloxymethyl-2-methylthiobicyclo<2.2.1>hept-5-ene-2-carboxylic Acid
• CAS No.: 139108-82-0
• Molecular Formula: C₁₇H₂₀O₃S
• Molecular Weight: 304.41
• Mol file: 139108-82-0.mol

Synonyms:7-Benzyloxymethyl-2-methylthiobicyclo<2.2.1>hept-5-ene-2-carboxylic Acid

Chemical Property of 7-Benzyloxymethyl-2-methylthiobicyclo<2.2.1>hept-5-ene-2-carboxylic Acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-Benzyloxymethyl-2-methylthiobicyclo<2.2.1>hept-5-ene-2-carboxylic Acid

There total 5 articles about 7-Benzyloxymethyl-2-methylthiobicyclo<2.2.1>hept-5-ene-2-carboxylic Acid 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: 87.0%

(1R,2R,4S,7R)-7-Benzyloxymethyl-2-methylsulfanyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester (139108-84-2) → 7-Benzyloxymethyl-2-methylthiobicyclo<2.2.1>hept-5-ene-2-carboxylic Acid (139108-82-0)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; at 110 ℃; for 4h;

DOI:10.1016/0040-4039(91)80522-8

Reference yield:

5-(benzyloxymethyl)cyclopentadiene (39939-07-6) → 7-Benzyloxymethyl-2-methylthiobicyclo<2.2.1>hept-5-ene-2-carboxylic Acid (139108-82-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / (-)-(S,S)-Al-catalyst / CH₂Cl₂ / 18 h / -78 °C

2: 100 percent / LiOH, aq. H₂O₂ / H₂O; tetrahydrofuran / 23 h / 23 °C

3: 1) MeSO₃H / 1) 2 h, 23 deg C, 2) 37 h, 23 deg C

4: 1) LDA / 1) hexane, DME, 2 h, 0 deg C, 2) -78 deg C, 1 h, then 0 deg C, 6 h

5: 87 percent / KOt-Bu / dimethylsulfoxide / 4 h / 110 °C

With lithium hydroxide; methanesulfonic acid; potassium tert-butylate; dihydrogen peroxide; lithium diisopropyl amide; (-)-(S,S)-Al-catalyst; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/0040-4039(91)80522-8

Reference yield:

Ethyl 7-Benzyloxymethylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylate (115219-37-9) → 7-Benzyloxymethyl-2-methylthiobicyclo<2.2.1>hept-5-ene-2-carboxylic Acid (139108-82-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) LDA / 1) hexane, DME, 2 h, 0 deg C, 2) -78 deg C, 1 h, then 0 deg C, 6 h

2: 87 percent / KOt-Bu / dimethylsulfoxide / 4 h / 110 °C

With potassium tert-butylate; lithium diisopropyl amide; In dimethyl sulfoxide;

DOI:10.1016/0040-4039(91)80522-8

upstream raw materials:

(1R,2R,4S,7R)-7-Benzyloxymethyl-2-methylsulfanyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester

5-(benzyloxymethyl)cyclopentadiene

Ethyl 7-Benzyloxymethylbicyclo<2.2.1>hept-5-ene-2-endo-carboxylate

(1R,2S,4S,7R)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Downstream raw materials:

(1R,4S,7R)-(-)-bicyclo <2.2.1> hept-7-benzyloxymethyl-5-ene-2-one