3-[(1R,2S,6S,7R)-7-(1-Benzyloxymethyl-vinyl)-2-methyl-bicyclo[4.1.0]hept-3-en-1-yl]-2-methoxy-3-oxo-propionic acid tert-butyl ester

Base Information

• Chemical Name: 3-[(1R,2S,6S,7R)-7-(1-Benzyloxymethyl-vinyl)-2-methyl-bicyclo[4.1.0]hept-3-en-1-yl]-2-methoxy-3-oxo-propionic acid tert-butyl ester
• CAS No.: 122690-80-6
• Molecular Formula: C₂₆H₃₄O₅
• Molecular Weight: 426.553
• Mol file: 122690-80-6.mol

Synonyms:

Chemical Property of 3-[(1R,2S,6S,7R)-7-(1-Benzyloxymethyl-vinyl)-2-methyl-bicyclo[4.1.0]hept-3-en-1-yl]-2-methoxy-3-oxo-propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(1R,2S,6S,7R)-7-(1-Benzyloxymethyl-vinyl)-2-methyl-bicyclo[4.1.0]hept-3-en-1-yl]-2-methoxy-3-oxo-propionic acid tert-butyl ester

There total 7 articles about 3-[(1R,2S,6S,7R)-7-(1-Benzyloxymethyl-vinyl)-2-methyl-bicyclo[4.1.0]hept-3-en-1-yl]-2-methoxy-3-oxo-propionic acid tert-butyl ester 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: 68.0%

2-methoxyacetic acid 1,1-dimethylethyl ester (17640-23-2) + (1S,2R,6R,7S)-7-(1-Benzyloxymethyl-vinyl)-2-methyl-bicyclo[4.1.0]hept-3-ene-1-carboxylic acid methyl ester (122690-79-3) → 3-[(1R,2S,6S,7R)-7-(1-Benzyloxymethyl-vinyl)-2-methyl-bicyclo[4.1.0]hept-3-en-1-yl]-2-methoxy-3-oxo-propionic acid tert-butyl ester (122690-80-6,122690-88-4)

Guidance literature:

With lithium diisopropyl amide;

DOI:10.1016/S0040-4039(00)82443-0

Reference yield:

(+/-)-3c-methyl-cyclohex-4-ene-1r,2c-dicarboxylic acid (15941-50-1,23667-61-0,40469-16-7,40469-17-8,40469-18-9,41792-44-3) → 3-[(1R,2S,6S,7R)-7-(1-Benzyloxymethyl-vinyl)-2-methyl-bicyclo[4.1.0]hept-3-en-1-yl]-2-methoxy-3-oxo-propionic acid tert-butyl ester (122690-80-6,122690-88-4)

Guidance literature:

Multi-step reaction with 7 steps

2: 86 percent / KOMe

3: 87 percent / PCC

4: 72 percent

5: 70 percent / SOCl₂

6: 88 percent / KOtBu

7: 68 percent / LDA

With thionyl chloride; potassium methanolate; potassium tert-butylate; pyridinium chlorochromate; lithium diisopropyl amide;

DOI:10.1016/S0040-4039(00)82443-0

Reference yield:

(3aR,7S,7aS)-7-Methyl-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one (122690-76-0) → 3-[(1R,2S,6S,7R)-7-(1-Benzyloxymethyl-vinyl)-2-methyl-bicyclo[4.1.0]hept-3-en-1-yl]-2-methoxy-3-oxo-propionic acid tert-butyl ester (122690-80-6,122690-88-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / KOMe

2: 87 percent / PCC

3: 72 percent

4: 70 percent / SOCl₂

5: 88 percent / KOtBu

6: 68 percent / LDA

With thionyl chloride; potassium methanolate; potassium tert-butylate; pyridinium chlorochromate; lithium diisopropyl amide;

DOI:10.1016/S0040-4039(00)82443-0

upstream raw materials:

2-methoxyacetic acid 1,1-dimethylethyl ester

(1S,2R,6R,7S)-7-(1-Benzyloxymethyl-vinyl)-2-methyl-bicyclo[4.1.0]hept-3-ene-1-carboxylic acid methyl ester

(+/-)-3c-methyl-cyclohex-4-ene-1r,2c-dicarboxylic acid

(3aR,7S,7aS)-7-Methyl-3a,4,7,7a-tetrahydro-3H-isobenzofuran-1-one

Downstream raw materials:

(4R,4aS,6R,9aR)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-oxo-1,4a,5,6,7,9a-hexahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl ester

(4R,4aR,6R,9aR)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-oxo-1,4a,5,6,7,9a-hexahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl ester

(4S,4aS,6R,9aS)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-oxo-1,4a,5,6,7,9a-hexahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl ester

(4R,6R,9aR)-8-Benzyloxymethyl-6-methoxy-4-methyl-5-trimethylsilanyloxy-1,6,7,9a-tetrahydro-4H-benzocycloheptene-6-carboxylic acid tert-butyl ester