α-(1'R,2'S,5'R)-8-(β-naphthyl)menthyl β-ethyl N-benzoyl-L-α-vinylaspartate

Base Information

Chemical Name:α-(1'R,2'S,5'R)-8-(β-naphthyl)menthyl β-ethyl N-benzoyl-L-α-vinylaspartate
CAS No.:278595-44-1
Molecular Formula:C₃₅H₄₁NO₅
Molecular Weight:555.714
Hs Code.:

Synonyms:α-(1'R,2'S,5'R)-8-(β-naphthyl)menthyl β-ethyl N-benzoyl-L-α-vinylaspartate

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Chemical Property of α-(1'R,2'S,5'R)-8-(β-naphthyl)menthyl β-ethyl N-benzoyl-L-α-vinylaspartate

Chemical Property:

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Technology Process of α-(1'R,2'S,5'R)-8-(β-naphthyl)menthyl β-ethyl N-benzoyl-L-α-vinylaspartate

There total 8 articles about α-(1'R,2'S,5'R)-8-(β-naphthyl)menthyl β-ethyl N-benzoyl-L-α-vinylaspartate 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:

: 105-36-2
ethyl bromoacetate

: 278595-59-8
(1'R,2'S,5'R)-8'-(β-naphthyl)menthyl N-benzoyl-(Z)-dehydrobutyrinate

: 278595-44-1
α-(1'R,2'S,5'R)-8-(β-naphthyl)menthyl β-ethyl N-benzoyl-L-α-vinylaspartate

: α-(1'R,2'S,5'R)-8'-(β-naphthyl)menthyl δ-ethyl N-benzoyldehydrohomoglutamate

Guidance literature:: With n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃;
DOI:10.1021/jo9918091

Reference yield:

: 105970-13-6
(1R,2S,5R)-8-(β-naphthyl)menthol

: 278595-44-1
α-(1'R,2'S,5'R)-8-(β-naphthyl)menthyl β-ethyl N-benzoyl-L-α-vinylaspartate

Guidance literature:: Multi-step reaction with 2 steps

1: 64 percent / p-TsOH / benzene / Heating

2: 110 mg / LDA; n-BuLi / hexamethylphosphoric acid triamide; hexane; tetrahydrofuran / -78 °C

With n-butyllithium; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; benzene; 1: Esterification / 2: Alkylation;
DOI:10.1021/jo9918091

Reference yield:

: 908093-98-1
diazodiphenylmethane

: 278595-44-1
α-(1'R,2'S,5'R)-8-(β-naphthyl)menthyl β-ethyl N-benzoyl-L-α-vinylaspartate

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaBH₄ / dimethylformamide / 1 h / 100 °C

1.2: 88 percent / ethyl acetate; hexane

2.1: 90 percent / O₃ / benzene; CH₂Cl₂; various solvent(s) / 1 h / Heating

3.1: 96 percent / TFA; anisole / CH₂Cl₂ / 3 h / 20 °C

4.1: 64 percent / p-TsOH / benzene / Heating

5.1: 110 mg / LDA; n-BuLi / hexamethylphosphoric acid triamide; hexane; tetrahydrofuran / -78 °C

With sodium tetrahydroborate; n-butyllithium; toluene-4-sulfonic acid; ozone; methoxybenzene; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: Ring cleavage / 1.2: Esterification / 2.1: ozonolysis / 3.1: Hydrolysis / 4.1: Esterification / 5.1: Alkylation;
DOI:10.1021/jo9918091