(2E,4S,5S,6S,7E)-2-bromo-6-ethyl-8-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-4-methyldeca-2,7-diene

Base Information

Chemical Name:(2E,4S,5S,6S,7E)-2-bromo-6-ethyl-8-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-4-methyldeca-2,7-diene
CAS No.:1330569-18-0
Molecular Formula:C₂₄H₃₇BrO₄
Molecular Weight:469.459
Hs Code.:

Synonyms:(2E,4S,5S,6S,7E)-2-bromo-6-ethyl-8-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-4-methyldeca-2,7-diene

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Chemical Property of (2E,4S,5S,6S,7E)-2-bromo-6-ethyl-8-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-4-methyldeca-2,7-diene

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Technology Process of (2E,4S,5S,6S,7E)-2-bromo-6-ethyl-8-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-4-methyldeca-2,7-diene

There total 11 articles about (2E,4S,5S,6S,7E)-2-bromo-6-ethyl-8-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-4-methyldeca-2,7-diene 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:

: 1170989-79-3
(2R,3R,4S,5E)-4-ethyl-6-(4-methoxybenzyloxymethyl)-3-methoxymethoxy-2-methyloct-5-enal

: 66070-35-7
(1,1-dibromoethyl)triphenylphosphonium bromide

: (2Z,4S,5S,6S,7E)-2-bromo-6-ethyl-8-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-4-methyldeca-2,7-diene

: 1330569-18-0
(2E,4S,5S,6S,7E)-2-bromo-6-ethyl-8-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-4-methyldeca-2,7-diene

Guidance literature:: (1,1-dibromoethyl)triphenylphosphonium bromide; With n-butyllithium; In diethyl ether; hexane; at -40 ℃; for 0.5h; Inert atmosphere;

(2R,3R,4S,5E)-4-ethyl-6-(4-methoxybenzyloxymethyl)-3-methoxymethoxy-2-methyloct-5-enal; In diethyl ether; hexane; at -78 ℃; for 0.333333h; optical yield given as %de; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2011.04.006

Reference yield:

: 1170989-57-7
ethyl (2E,4S)-4-(tert-butyldimethylsilyloxy)methyl-2-ethyl-hex-2-enoate

: (2Z,4S,5S,6S,7E)-2-bromo-6-ethyl-8-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-4-methyldeca-2,7-diene

: 1330569-18-0
(2E,4S,5S,6S,7E)-2-bromo-6-ethyl-8-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-4-methyldeca-2,7-diene

Guidance literature:: Multi-step reaction with 9 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.67 h / -78 °C / Inert atmosphere

1.2: 3.5 h / -78 - 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

2.2: 21 h / 0 - 20 °C

3.1: acetic acid / tetrahydrofuran; water / 21.5 h / 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.2: 1 h / -78 - 20 °C / Inert atmosphere

5.1: n-butyllithium; potassium tert-butylate / tetrahydrofuran; hexane / 0.25 h / -100 - -50 °C / Inert atmosphere

5.2: 0.5 h / -100 - -78 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 14 h / Reflux

7.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 9.5 h / 20 °C

8.1: sodium periodate / water; acetone / 0.83 h / 0 - 20 °C

9.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -40 °C / Inert atmosphere

9.2: 0.33 h / -78 °C / Inert atmosphere

With sodium periodate; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; potassium tert-butylate; water; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; mineral oil; tert-butyl alcohol; 4.1: Swern oxidation / 4.2: Swern oxidation / 9.2: Wittig reaction;
DOI:10.1016/j.tet.2011.04.006

Reference yield:

: 1170989-60-2
(2E,4S)-4-(tert-butyldimethylsilyloxymethyl)-2-ethylhex-2-en-1-ol

: (2Z,4S,5S,6S,7E)-2-bromo-6-ethyl-8-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-4-methyldeca-2,7-diene

: 1330569-18-0
(2E,4S,5S,6S,7E)-2-bromo-6-ethyl-8-(4-methoxybenzyloxy)methyl-5-methoxymethoxy-4-methyldeca-2,7-diene

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

1.2: 21 h / 0 - 20 °C

2.1: acetic acid / tetrahydrofuran; water / 21.5 h / 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 - 20 °C / Inert atmosphere

4.1: n-butyllithium; potassium tert-butylate / tetrahydrofuran; hexane / 0.25 h / -100 - -50 °C / Inert atmosphere

4.2: 0.5 h / -100 - -78 °C / Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 14 h / Reflux

6.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 9.5 h / 20 °C

7.1: sodium periodate / water; acetone / 0.83 h / 0 - 20 °C

8.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -40 °C / Inert atmosphere

8.2: 0.33 h / -78 °C / Inert atmosphere

With sodium periodate; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; potassium tert-butylate; water; sodium hydride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; mineral oil; tert-butyl alcohol; 3.1: Swern oxidation / 3.2: Swern oxidation / 8.2: Wittig reaction;
DOI:10.1016/j.tet.2011.04.006