(3aR,4S,5S,7aS)-5,7a-Dihydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester

Base Information

• Chemical Name: (3aR,4S,5S,7aS)-5,7a-Dihydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester
• CAS No.: 144066-90-0
• Molecular Formula: C₁₂H₁₆O₆
• Molecular Weight: 256.255
• Mol file: 144066-90-0.mol

Synonyms:(3aR,4S,5S,7aS)-5,7a-Dihydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester

Chemical Property of (3aR,4S,5S,7aS)-5,7a-Dihydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,5S,7aS)-5,7a-Dihydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester

There total 1 articles about (3aR,4S,5S,7aS)-5,7a-Dihydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl 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:

3-hydroxy-2-pyrone (496-64-0) + 4-hydroxy-2-methylbut-2-enoic acid ethyl ester (90177-85-8) → (3aR,4S,5S,7aS)-5,7a-Dihydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester (144066-90-0)

Guidance literature:

With 2,2-Dimethyl-1,3-propanediol; phenylboronic acid; Yield given. Multistep reaction; 1.) benzene, 90 deg C, 48 h, 2.) benzene, 25 deg C, 30 min;

DOI:10.1039/c39920001118

Reference yield: 80.0%

benzyl bromide (100-39-0) + (3aR,4S,5S,7aS)-5,7a-Dihydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester (144066-90-0) → (1R,4R,5S,6R)-4-Benzyloxy-5-benzyloxymethyl-6-methyl-3-oxo-2-oxa-bicyclo[2.2.2]oct-7-ene-6-carboxylic acid ethyl ester (144066-91-1)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium hydride; In tetrahydrofuran; at 0 - 25 ℃; for 1.5h;

DOI:10.1039/c39920001118

Reference yield: 75.0%

benzyl bromide (100-39-0) + (3aR,4S,5S,7aS)-5,7a-Dihydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester (144066-90-0) → (3aS,4R,5R,7aR)-5,7a-Bis-benzyloxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium hydride; at 0 - 25 ℃; for 2h;

DOI:10.1021/ja00107a007

upstream raw materials:

3-hydroxy-2-pyrone

4-hydroxy-2-methylbut-2-enoic acid ethyl ester

Downstream raw materials:

(1R,4R,5S,6R)-4-Benzyloxy-5-benzyloxymethyl-6-methyl-3-oxo-2-oxa-bicyclo[2.2.2]oct-7-ene-6-carboxylic acid ethyl ester