(3S,4E)-3-methyl-7-benzyloxy-4-heptenoic acid ethyl ester

Base Information

Chemical Name:(3S,4E)-3-methyl-7-benzyloxy-4-heptenoic acid ethyl ester
CAS No.:214483-92-8
Molecular Formula:C₁₇H₂₄O₃
Molecular Weight:276.376
Hs Code.:

Synonyms:(3S,4E)-3-methyl-7-benzyloxy-4-heptenoic acid ethyl ester

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Chemical Property of (3S,4E)-3-methyl-7-benzyloxy-4-heptenoic acid ethyl ester

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Technology Process of (3S,4E)-3-methyl-7-benzyloxy-4-heptenoic acid ethyl ester

There total 3 articles about (3S,4E)-3-methyl-7-benzyloxy-4-heptenoic acid ethyl 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: 96.0%

: 78-39-7
Triethyl orthoacetate

: 214483-91-7
(S,E)-1-(benzyloxy)hex-4-en-3-ol

: 214483-92-8
(3S,4E)-3-methyl-7-benzyloxy-4-heptenoic acid ethyl ester

Guidance literature:: With propionic acid; at 140 ℃;
DOI:10.1021/jo981181e

Reference yield:

: 214483-90-6
(3S)-1-benzyloxy-4-hexyn-3-ol

: 214483-92-8
(3S,4E)-3-methyl-7-benzyloxy-4-heptenoic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / LAH / tetrahydrofuran / 4 h / Heating

2: 92 percent / propionic acid / 26 h / 145 °C

With lithium aluminium tetrahydride; propionic acid; In tetrahydrofuran;
DOI:10.1016/S0040-4020(02)00050-9

Reference yield:

: 85960-55-0
(S)-(2-phenylmethoxyethyl)oxirane

: 214483-92-8
(3S,4E)-3-methyl-7-benzyloxy-4-heptenoic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: dimethylsulfoxide / 15 - 20 °C

1.2: 85 percent / KOt-Bu / dimethylsulfoxide / 15 °C

2.1: 96 percent / LiH / tetrahydrofuran / Heating

3.1: 96 percent / C₂H₅CO₂H / 140 °C

With lithium hydride; propionic acid; In tetrahydrofuran; dimethyl sulfoxide; 1.1: Substitution / 1.2: Isomerization / 2.1: Reduction / 3.1: Claisen rearrangement;
DOI:10.1021/jo981181e