ethyl (+/-)-erythro-9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(1-methyl-1H-tetrazol-5-yl)-6,8-nonadienoate

Base Information

• Chemical Name: ethyl (+/-)-erythro-9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(1-methyl-1H-tetrazol-5-yl)-6,8-nonadienoate
• CAS No.: 118874-96-7
• Molecular Formula: C₂₅H₂₆F₂N₄O₄
• Molecular Weight: 484.503
• Mol file: 118874-96-7.mol

Synonyms:

Chemical Property of ethyl (+/-)-erythro-9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(1-methyl-1H-tetrazol-5-yl)-6,8-nonadienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (+/-)-erythro-9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(1-methyl-1H-tetrazol-5-yl)-6,8-nonadienoate

There total 10 articles about ethyl (+/-)-erythro-9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(1-methyl-1H-tetrazol-5-yl)-6,8-nonadienoate 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: 75.0%

ethyl 9,9-bis(4-fluorophenyl)-5-hydroxy-8-(1-methyl-1H-tetrazol-5-yl)-3-oxo-6,8-nonadienoate (130273-24-4) → ethyl (+/-)-erythro-9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(1-methyl-1H-tetrazol-5-yl)-6,8-nonadienoate (118874-96-7,118875-42-6,130273-25-5)

Guidance literature:

With sodium tetrahydroborate; triethyl borane; In tetrahydrofuran; methanol; at -78 ℃;

DOI:10.1021/jm00129a004

Reference yield:

4,4'-Difluorobenzophenone (345-92-6) → ethyl (+/-)-erythro-9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(1-methyl-1H-tetrazol-5-yl)-6,8-nonadienoate (118874-96-7,118875-42-6,130273-25-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) n-BuLi / 1) THF, -78 deg C

2: p-TsOH / toluene / Heating

3: 65 percent

4: 1) NaH, n-BuLi / 1) THF, -20 deg C

5: 75 percent / NaBH₄, BEt₃ / tetrahydrofuran; methanol / -78 °C

With sodium tetrahydroborate; n-butyllithium; triethyl borane; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; toluene;

DOI:10.1021/jm00129a004

Reference yield:

1,1-bis(4-fluorophenyl)-2-(1-methyl-1H-tetrazol-5-yl)ethene (118875-66-4) → ethyl (+/-)-erythro-9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(1-methyl-1H-tetrazol-5-yl)-6,8-nonadienoate (118874-96-7,118875-42-6,130273-25-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent

2: 1) NaH, n-BuLi / 1) THF, -20 deg C

3: 75 percent / NaBH₄, BEt₃ / tetrahydrofuran; methanol / -78 °C

With sodium tetrahydroborate; n-butyllithium; triethyl borane; sodium hydride; In tetrahydrofuran; methanol;

DOI:10.1021/jm00129a004

upstream raw materials:

ethyl 9,9-bis(4-fluorophenyl)-5-hydroxy-8-(1-methyl-1H-tetrazol-5-yl)-3-oxo-6,8-nonadienoate

5-[2,2-bis(4-fluorophenyl)-1-methylethenyl]-1-methyl-1H-tetrazole

3,3-bis(4-fluorophenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenal

3,3-bis(4-fluorophenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenol

Downstream raw materials:

sodium (+/-)-erythro-9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(1-methyl-1H-tetrazol-5-yl)-6,8-nonadienoate

(+/-)-erythro-9,9-bis(4-fluorophenyl)-3,5-dihydroxy-8-(1-methyl-1H-tetrazol-5-yl)-6,8-nonadienoic acid

trans-6-<4,4-bis(4-fluorophenyl)-3-(1-methyl-1H-tetrazol-5-yl)-1,3-butadienyl>tetrahydro-4-hydroxy-2H-pyran-2-one

Refernces

• 1、 Balasubramanian, N.,Brown, P. J.,Catt, J. D.,Han, W. T.,Parker, R. A.,et al.. "A Potent, Tissue-Selective, Synthetic Inhibitor of HMG-CoA Reductase". . p. 2038 - 2041. Retrieved 2007/10/02.