(R)-(3E,6S,7R,8R,9Z)-8-hydroxy-12-(3-(methoxymethoxy)-5-nitrophenyl)-7,9-dimethyldodeca-1,3,9-trien-6-yl 2-(cyclohexanecarboxamido)propanoate

Base Information

Chemical Name:(R)-(3E,6S,7R,8R,9Z)-8-hydroxy-12-(3-(methoxymethoxy)-5-nitrophenyl)-7,9-dimethyldodeca-1,3,9-trien-6-yl 2-(cyclohexanecarboxamido)propanoate
CAS No.:1447811-45-1
Molecular Formula:C₃₂H₄₆N₂O₈
Molecular Weight:586.726
Hs Code.:

Synonyms:(R)-(3E,6S,7R,8R,9Z)-8-hydroxy-12-(3-(methoxymethoxy)-5-nitrophenyl)-7,9-dimethyldodeca-1,3,9-trien-6-yl 2-(cyclohexanecarboxamido)propanoate

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Chemical Property of (R)-(3E,6S,7R,8R,9Z)-8-hydroxy-12-(3-(methoxymethoxy)-5-nitrophenyl)-7,9-dimethyldodeca-1,3,9-trien-6-yl 2-(cyclohexanecarboxamido)propanoate

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Technology Process of (R)-(3E,6S,7R,8R,9Z)-8-hydroxy-12-(3-(methoxymethoxy)-5-nitrophenyl)-7,9-dimethyldodeca-1,3,9-trien-6-yl 2-(cyclohexanecarboxamido)propanoate

There total 12 articles about (R)-(3E,6S,7R,8R,9Z)-8-hydroxy-12-(3-(methoxymethoxy)-5-nitrophenyl)-7,9-dimethyldodeca-1,3,9-trien-6-yl 2-(cyclohexanecarboxamido)propanoate 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%

: 1447811-37-1
(R)-((3E,6S,7S,8R,9Z)-8-(4-methoxybenzyloxy)-12-(3-(methoxymethoxy)-5-nitrophenyl)-7,9-dimethyldodeca-1,3,9-trien-6-yl) 2-(cyclohexanecarboxamido)propanoate

: 1447811-45-1
(R)-(3E,6S,7R,8R,9Z)-8-hydroxy-12-(3-(methoxymethoxy)-5-nitrophenyl)-7,9-dimethyldodeca-1,3,9-trien-6-yl 2-(cyclohexanecarboxamido)propanoate

Guidance literature:: With dimethylsulfide; magnesium bromide diethyl etherate; 1,3-Dimethoxybenzene; In dichloromethane; at 0 - 25 ℃; for 6h; Inert atmosphere;
DOI:10.1021/ja4061273

Reference yield:

: 1447811-40-6
(Z)-tert-butyl(5-(3-(methoxymethoxy)-5-nitrophenyl)-2-methylpent-2-enyloxy)dimethylsilane

: 1447811-45-1
(R)-(3E,6S,7R,8R,9Z)-8-hydroxy-12-(3-(methoxymethoxy)-5-nitrophenyl)-7,9-dimethyldodeca-1,3,9-trien-6-yl 2-(cyclohexanecarboxamido)propanoate

Guidance literature:: Multi-step reaction with 9 steps

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

2.1: (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

2.2: 3 h / 80 °C / Inert atmosphere

3.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; dimethyl sulfoxide / 3 h / 0 - 25 °C / Inert atmosphere

4.1: osmium(VIII) oxide; sodium periodate; 2,6-dimethylpyridine / water; 1,4-dioxane; tert-butyl alcohol / 17.5 h / 25 °C / Inert atmosphere

5.1: dimethylaluminum chloride / dichloromethane; hexane / 0.03 h / -78 °C / Inert atmosphere

5.2: 0.08 h / -78 °C / Inert atmosphere

6.1: dicyclohexyl-carbodiimide / dichloromethane / 1 h / 0 - 25 °C / Inert atmosphere; Molecular sieve

6.2: 3 h / -78 °C / Inert atmosphere

7.1: piperidine / tetrahydrofuran / 0.5 h / 0 - 25 °C / Inert atmosphere

8.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 14 h / 0 - 25 °C / Inert atmosphere

9.1: magnesium bromide diethyl etherate; dimethylsulfide; 1,3-Dimethoxybenzene / dichloromethane / 6 h / 0 - 25 °C / Inert atmosphere

With piperidine; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); dimethylsulfide; (R)-(+)-5,5′-bis[di(3,5-xylyl)phosphino]-4,4′-bi-1,3-benzodioxole; tetrabutyl ammonium fluoride; dimethylaluminum chloride; magnesium bromide diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 1,3-Dimethoxybenzene; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; tert-butyl alcohol;
DOI:10.1021/ja4061273

Reference yield:

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

: 1447811-45-1
(R)-(3E,6S,7R,8R,9Z)-8-hydroxy-12-(3-(methoxymethoxy)-5-nitrophenyl)-7,9-dimethyldodeca-1,3,9-trien-6-yl 2-(cyclohexanecarboxamido)propanoate

Guidance literature:: Multi-step reaction with 10 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

4.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; dimethyl sulfoxide / 3 h / 0 - 25 °C / Inert atmosphere

5.1: osmium(VIII) oxide; sodium periodate; 2,6-dimethylpyridine / water; 1,4-dioxane; tert-butyl alcohol / 17.5 h / 25 °C / Inert atmosphere

6.1: dimethylaluminum chloride / dichloromethane; hexane / 0.03 h / -78 °C / Inert atmosphere

6.2: 0.08 h / -78 °C / Inert atmosphere

7.1: dicyclohexyl-carbodiimide / dichloromethane / 1 h / 0 - 25 °C / Inert atmosphere; Molecular sieve

7.2: 3 h / -78 °C / Inert atmosphere

8.1: piperidine / tetrahydrofuran / 0.5 h / 0 - 25 °C / Inert atmosphere

9.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 14 h / 0 - 25 °C / Inert atmosphere

10.1: magnesium bromide diethyl etherate; dimethylsulfide; 1,3-Dimethoxybenzene / dichloromethane / 6 h / 0 - 25 °C / Inert atmosphere

With piperidine; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); dimethylsulfide; (R)-(+)-5,5′-bis[di(3,5-xylyl)phosphino]-4,4′-bi-1,3-benzodioxole; tetrabutyl ammonium fluoride; dimethylaluminum chloride; magnesium bromide diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; dicyclohexyl-carbodiimide; 1,3-Dimethoxybenzene; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; tert-butyl alcohol; 1.2: |Suzuki Coupling;
DOI:10.1021/ja4061273