(3S,4R,Z)-8-(3-(methoxymethoxy)-5-nitrophenyl)-3,5-dimethylocta-1,5-dien-4-ol

Base Information

Chemical Name:(3S,4R,Z)-8-(3-(methoxymethoxy)-5-nitrophenyl)-3,5-dimethylocta-1,5-dien-4-ol
CAS No.:1447811-35-9
Molecular Formula:C₁₈H₂₅NO₅
Molecular Weight:335.4
Hs Code.:

Synonyms:(3S,4R,Z)-8-(3-(methoxymethoxy)-5-nitrophenyl)-3,5-dimethylocta-1,5-dien-4-ol

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Chemical Property of (3S,4R,Z)-8-(3-(methoxymethoxy)-5-nitrophenyl)-3,5-dimethylocta-1,5-dien-4-ol

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Technology Process of (3S,4R,Z)-8-(3-(methoxymethoxy)-5-nitrophenyl)-3,5-dimethylocta-1,5-dien-4-ol

There total 5 articles about (3S,4R,Z)-8-(3-(methoxymethoxy)-5-nitrophenyl)-3,5-dimethylocta-1,5-dien-4-ol 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:

: 1447811-34-8
(Z)-5-(3-(methoxymethoxy)-5-nitrophenyl)-2-methylpent-2-en-1-ol

: 103223-44-5
(buta-1,3-dien-2-yl)dimethyl(phenyl)silane

: 1447811-35-9
(3S,4R,Z)-8-(3-(methoxymethoxy)-5-nitrophenyl)-3,5-dimethylocta-1,5-dien-4-ol

: (Z)-8-(3-(methoxymethoxy)-5-nitrophenyl)-3,5-dimethylocta-1,5-dien-4-ol

: (E)-8-(3-(methoxymethoxy)-5-nitrophenyl)-3,5-dimethylocta-1,5-dien-4-ol

Guidance literature:: (Z)-5-(3-(methoxymethoxy)-5-nitrophenyl)-2-methylpent-2-en-1-ol; (buta-1,3-dien-2-yl)dimethyl(phenyl)silane; With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); (R)-(+)-5,5′-bis[di(3,5-xylyl)phosphino]-4,4′-bi-1,3-benzodioxole; In ethyl acetate; at 95 ℃; for 16h; Inert atmosphere;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dimethyl sulfoxide; ethyl acetate; at 80 ℃; for 3h; Overall yield = 64 %; Overall yield = 460 mg; enantioselective reaction; Inert atmosphere;
DOI:10.1021/ja4061273

Reference yield:

: 116632-23-6
3-bromo-5-nitro-phenol

: 1447811-35-9
(3S,4R,Z)-8-(3-(methoxymethoxy)-5-nitrophenyl)-3,5-dimethylocta-1,5-dien-4-ol

: (Z)-8-(3-(methoxymethoxy)-5-nitrophenyl)-3,5-dimethylocta-1,5-dien-4-ol

: (E)-8-(3-(methoxymethoxy)-5-nitrophenyl)-3,5-dimethylocta-1,5-dien-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / tetrahydrofuran; water / 16 h / 100 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / diethyl ether; toluene / 14 h / 0 - 25 °C / Inert atmosphere

3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 25 °C / Inert atmosphere

3.2: 14 h / 0 - 25 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 25 °C / Inert atmosphere

5.1: (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); (R)-(+)-5,5′-bis[di(3,5-xylyl)phosphino]-4,4′-bi-1,3-benzodioxole / ethyl acetate / 16 h / 95 °C / Inert atmosphere

5.2: 3 h / 80 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); (R)-(+)-5,5′-bis[di(3,5-xylyl)phosphino]-4,4′-bi-1,3-benzodioxole; tetrabutyl ammonium fluoride; potassium carbonate; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; In tetrahydrofuran; diethyl ether; water; ethyl acetate; toluene; 1.1: |Suzuki Coupling / 3.2: |Suzuki Coupling;
DOI:10.1021/ja4061273

Reference yield:

: 1447811-32-6
1-(methoxymethoxy)-3-nitro-5-vinylbenzene

: 1447811-35-9
(3S,4R,Z)-8-(3-(methoxymethoxy)-5-nitrophenyl)-3,5-dimethylocta-1,5-dien-4-ol

: (Z)-8-(3-(methoxymethoxy)-5-nitrophenyl)-3,5-dimethylocta-1,5-dien-4-ol

: (E)-8-(3-(methoxymethoxy)-5-nitrophenyl)-3,5-dimethylocta-1,5-dien-4-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 25 °C / Inert atmosphere

1.2: 14 h / 0 - 25 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 25 °C / Inert atmosphere

3.1: (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); (R)-(+)-5,5′-bis[di(3,5-xylyl)phosphino]-4,4′-bi-1,3-benzodioxole / ethyl acetate / 16 h / 95 °C / Inert atmosphere

3.2: 3 h / 80 °C / Inert atmosphere

With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); (R)-(+)-5,5′-bis[di(3,5-xylyl)phosphino]-4,4′-bi-1,3-benzodioxole; tetrabutyl ammonium fluoride; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; ethyl acetate; 1.2: |Suzuki Coupling;
DOI:10.1021/ja4061273