(E)-(3S,4S)-2-Formyl-4-methoxy-3-methyl-6-phenyl-hex-5-enoic acid methyl ester

Base Information

Chemical Name:(E)-(3S,4S)-2-Formyl-4-methoxy-3-methyl-6-phenyl-hex-5-enoic acid methyl ester
CAS No.:90664-08-7
Molecular Formula:C₁₆H₂₀O₄
Molecular Weight:276.332
Hs Code.:

Synonyms:(E)-(3S,4S)-2-Formyl-4-methoxy-3-methyl-6-phenyl-hex-5-enoic acid methyl ester

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Chemical Property of (E)-(3S,4S)-2-Formyl-4-methoxy-3-methyl-6-phenyl-hex-5-enoic acid methyl ester

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Technology Process of (E)-(3S,4S)-2-Formyl-4-methoxy-3-methyl-6-phenyl-hex-5-enoic acid methyl ester

There total 23 articles about (E)-(3S,4S)-2-Formyl-4-methoxy-3-methyl-6-phenyl-hex-5-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:

: 88644-08-0
(3S,4R,E)-methyl 4-methoxy-3-methyl-6-phenylhex-5-enoate

: 3197-61-3
N-formylimidazole

: 90664-08-7
(E)-(3S,4S)-2-Formyl-4-methoxy-3-methyl-6-phenyl-hex-5-enoic acid methyl ester

Guidance literature:: (3S,4R,E)-methyl 4-methoxy-3-methyl-6-phenylhex-5-enoate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.333333h; Inert atmosphere;

N-formylimidazole; In tetrahydrofuran; at -78 - 20 ℃; for 2.5h; Inert atmosphere;
DOI:10.1016/j.tetasy.2017.06.002

Reference yield:

: 107-31-3
Methyl formate

: 88644-08-0
(3S,4R,E)-methyl 4-methoxy-3-methyl-6-phenylhex-5-enoate

: 90664-08-7
(E)-(3S,4S)-2-Formyl-4-methoxy-3-methyl-6-phenyl-hex-5-enoic acid methyl ester

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 0 ℃;
DOI:10.1016/S0040-4039(00)81829-8

Reference yield:

: 2959-74-2
benzyldiphenylphosphine oxide

: 90664-08-7
(E)-(3S,4S)-2-Formyl-4-methoxy-3-methyl-6-phenyl-hex-5-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: MgBr₂*Et₂O, n-BuLi / tetrahydrofuran; hexane / -78 °C

2: LiBH₄ / tetrahydrofuran / 0 - 20 °C

3: 1.) 9-BBN, 2.) 15percent aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, from 0 deg C to RT, overnight, 2.) THF, EtOH, 4 h

4: 100 percent / 8 N Jones reagent / acetone / 2 h

6: 1.) LDA / 1.) THF, -78 deg C, 5 min, 2.) THF, from -78 to RT, 35 min

With sodium hydroxide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; jones reagent; dihydrogen peroxide; magnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; hexane; acetone;
DOI:10.1021/jo00228a028