(+)-E-(2R,3S)-5-methoxy-4-methyl-3-oxo-7-phenyl-hept-6-enoic acid methyl ester

Base Information

Chemical Name:(+)-E-(2R,3S)-5-methoxy-4-methyl-3-oxo-7-phenyl-hept-6-enoic acid methyl ester
CAS No.:910131-53-2
Molecular Formula:C₁₆H₂₀O₄
Molecular Weight:276.332
Hs Code.:

Synonyms:(+)-E-(2R,3S)-5-methoxy-4-methyl-3-oxo-7-phenyl-hept-6-enoic acid methyl ester

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Chemical Property of (+)-E-(2R,3S)-5-methoxy-4-methyl-3-oxo-7-phenyl-hept-6-enoic acid methyl ester

Chemical Property:

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Technology Process of (+)-E-(2R,3S)-5-methoxy-4-methyl-3-oxo-7-phenyl-hept-6-enoic acid methyl ester

There total 9 articles about (+)-E-(2R,3S)-5-methoxy-4-methyl-3-oxo-7-phenyl-hept-6-enoic acid methyl 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: 85.0%

: 88644-06-8
(+)-E-(2R,3S)-3-methoxy-2-methyl-5-phenyl-pent-4-enoic acid

: 79-20-9
acetic acid methyl ester

: 910131-53-2
(+)-E-(2R,3S)-5-methoxy-4-methyl-3-oxo-7-phenyl-hept-6-enoic acid methyl ester

Guidance literature:: acetic acid methyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

(+)-E-(2R,3S)-3-methoxy-2-methyl-5-phenyl-pent-4-enoic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃; for 2h;

In tetrahydrofuran; at -78 - 0 ℃; for 3h; Further stages.;
DOI:10.1039/b603433k

Reference yield:

: 478011-21-1
(E)-(4S,5S)-3-Hydroxy-5-methoxy-4-methyl-7-phenyl-hept-6-enoic acid methyl ester

: 910131-53-2
(+)-E-(2R,3S)-5-methoxy-4-methyl-3-oxo-7-phenyl-hept-6-enoic acid methyl ester

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/S0960-894X(02)00625-X

Reference yield:

: 14371-10-9
(E)-3-phenylpropenal

: 910131-53-2
(+)-E-(2R,3S)-5-methoxy-4-methyl-3-oxo-7-phenyl-hept-6-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-Bu₂BOTf; Et₃N / CH₂Cl₂ / 1 h / 0 °C

1.2: CH₂Cl₂ / 2.33 h / -78 - 0 °C

1.3: 90 percent / aq. H₂O₂ / CH₂Cl₂; methanol / 10 °C

2.1: 72 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 40 h / 20 °C

3.1: 80 percent / aq. H₂O₂; LiOH / tetrahydrofuran / 4 h / 0 °C

4.1: LDA / tetrahydrofuran / -78 °C

4.2: N,N'-carbonyldiimidazole / tetrahydrofuran / 2 h / 20 °C

4.3: 85 percent / tetrahydrofuran / 3 h / -78 - 0 °C

With lithium hydroxide; 2,6-di-tert-butyl-pyridine; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1.2: Evans aldol reaction;
DOI:10.1039/b603433k