(E)-(4S,5S)-4-[3-(4-Methoxy-benzyloxy)-propyl]-5-methyl-octa-1,6-dien-3-one

Base Information

Chemical Name:(E)-(4S,5S)-4-[3-(4-Methoxy-benzyloxy)-propyl]-5-methyl-octa-1,6-dien-3-one
CAS No.:896104-52-2
Molecular Formula:C₂₀H₂₈O₃
Molecular Weight:316.441
Hs Code.:

Synonyms:(E)-(4S,5S)-4-[3-(4-Methoxy-benzyloxy)-propyl]-5-methyl-octa-1,6-dien-3-one

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Chemical Property of (E)-(4S,5S)-4-[3-(4-Methoxy-benzyloxy)-propyl]-5-methyl-octa-1,6-dien-3-one

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Technology Process of (E)-(4S,5S)-4-[3-(4-Methoxy-benzyloxy)-propyl]-5-methyl-octa-1,6-dien-3-one

There total 2 articles about (E)-(4S,5S)-4-[3-(4-Methoxy-benzyloxy)-propyl]-5-methyl-octa-1,6-dien-3-one 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: 82.0%

: 896104-74-8
(2S,3S,4E)-N-methoxy-2-{3-[(4-methoxybenzyl)oxy]propyl}-N,3-dimethylhex-4-enamide

: 1826-67-1
vinyl magnesium bromide

: 896104-52-2
(E)-(4S,5S)-4-[3-(4-Methoxy-benzyloxy)-propyl]-5-methyl-octa-1,6-dien-3-one

Guidance literature:: In tetrahydrofuran; at 20 ℃;
DOI:10.1021/jo0604585

Reference yield:

: 896104-51-1
(E)-(2S,3S)-2-[3-(4-Methoxy-benzyloxy)-propyl]-3-methyl-hex-4-enoic acid

: 896104-52-2
(E)-(4S,5S)-4-[3-(4-Methoxy-benzyloxy)-propyl]-5-methyl-octa-1,6-dien-3-one

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / MsCl; Et₃N / tetrahydrofuran / 1 h / 0 °C

2: 82 percent / tetrahydrofuran / 20 °C

With methanesulfonyl chloride; triethylamine; In tetrahydrofuran;
DOI:10.1021/jo0604585

Reference yield:

: 896104-52-2
(E)-(4S,5S)-4-[3-(4-Methoxy-benzyloxy)-propyl]-5-methyl-octa-1,6-dien-3-one

: (2Z,11E)-(5S,6R,9S,15S,16S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-isopropyl-9,12,16-trimethyl-tricyclo[13.3.0.0^5,9]octadeca-1⁽¹⁸⁾,2,11-trien-10-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: Grubbs catalyst / CH₂Cl₂ / Heating

2.1: H₂ / Pd/C / ethyl acetate / 2 h

3.1: LHMDS / toluene / 1 h / -78 °C

3.2: tetrahydrofuran / 4 h / -78 - 20 °C

4.1: HSnBu₃; Pd(PPh₃)4 / tetrahydrofuran / 2 h

4.2: 1.18 percent / Pd(PPh₃)4; LiCl; CuCl / dimethylsulfoxide / 37 h / 60 °C

5.1: 87 percent / DIBAL-H / CH₂Cl₂ / -78 - 20 °C

6.1: 93 percent / imidazole / dimethylformamide / 18 h / 20 °C

7.1: 91 percent / catecholborane bromide; 2,6-lutidine / CH₂Cl₂ / 7 h / 0 °C

8.1: 87 percent / Dess-Martin periodinane; 2,6-lutidine / CH₂Cl₂ / 2 h

9.1: 96 percent / K₂CO₃ / methanol / 20 °C

10.1: 77 percent / PdCl₂(CH₃CN)2 / acetone; H₂O / 40 h / Heating

11.1: Zp₂ZrCl₂ / CH₂Cl₂ / 13 h / 20 °C

11.2: 82 percent / I₂ / CH₂Cl₂ / -30 - 30 °C

12.1: 90 percent / Dess-Martin periodinane; 2,6-lutidine / CH₂Cl₂ / 1 h

13.1: 35 percent / NiCl₂; CrCl₂ / tetrahydrofuran; dimethylsulfoxide / 42 h

14.1: 81 percent / Dess-Martin periodinane; 2,6-lutidine / CH₂Cl₂ / 1 h

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; dichloro bis(acetonitrile) palladium(II); Grubbs catalyst first generation; tetrakis(triphenylphosphine) palladium⁽⁰⁾; zirconocene dichloride; bromocatecholborane; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; nickel dichloride; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; 4.2: Stille coupling / 8.1: Dess-Martin oxidation / 12.1: Dess-Martin oxidation / 13.1: Kishi-Nozaki-Hiyama carbonyl addition reaction / 14.1: Dess-Martin oxidation;
DOI:10.1021/jo0604585