tert-butyl (R,E)-5-benzylidene-2-ethyl-4-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate

Base Information

• Chemical Name: tert-butyl (R,E)-5-benzylidene-2-ethyl-4-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate
• CAS No.: 864516-20-1
• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.408

Synonyms:tert-butyl (R,E)-5-benzylidene-2-ethyl-4-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate

Chemical Property of tert-butyl (R,E)-5-benzylidene-2-ethyl-4-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate

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Technology Process of tert-butyl (R,E)-5-benzylidene-2-ethyl-4-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate

There total 3 articles about tert-butyl (R,E)-5-benzylidene-2-ethyl-4-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate 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:

tert-butyl (3R)-3-methyl-5-oxo-2-propionyl-5-(2-thioxothiazolidin-3-yl)pentanoate (864515-91-3) → tert-butyl (R,E)-5-benzylidene-2-ethyl-4-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate (864516-20-1)

Guidance literature:

Multi-step reaction with 2 steps

1: DBU / CH₂Cl₂ / 0 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1021/ja053820q

Reference yield:

t-Butyl 3-oxopentanoate (33400-61-2) → tert-butyl (R,E)-5-benzylidene-2-ethyl-4-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate (864516-20-1)

Guidance literature:

Multi-step reaction with 3 steps

1: [Ni((S)-Tol-BINAP)]OTf₂ / ethyl acetate / 14 h / 0 °C

2: DBU / CH₂Cl₂ / 0 °C

With [Ni((S)-Tol-BINAP)]OTf₂; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; ethyl acetate; 1: MIchael reaction;

DOI:10.1021/ja053820q

Reference yield:

tert-butyl (R)-2-ethyl-4-dimethyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate (864515-97-9) + benzaldehyde (100-52-7) → tert-butyl (R,E)-5-benzylidene-2-ethyl-4-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate (864516-20-1) + tert-butyl (R,Z)-5-benzylidene-2-ethyl-4-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate

Guidance literature:

Multistep reaction. Title compound not separated from byproducts;

DOI:10.1021/ja053820q

upstream raw materials:

tert-butyl (R)-2-ethyl-4-dimethyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate

benzaldehyde

tert-butyl (3R)-3-methyl-5-oxo-2-propionyl-5-(2-thioxothiazolidin-3-yl)pentanoate

t-Butyl 3-oxopentanoate

Downstream raw materials:

tert-butyl (4R,5S)-5-benzyl-2-ethyl-4-methyl-6-oxo-5,6-dihydro-4H-pyran-3-carboxylate

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