rel-(1R,2R)-(5E,9E,13E)-2-isopropyl-5,9,13-trimethyl-5,9,13-cyclotetradecatrienyl (benzyloxy)methyl ether

Base Information

Chemical Name:rel-(1R,2R)-(5E,9E,13E)-2-isopropyl-5,9,13-trimethyl-5,9,13-cyclotetradecatrienyl (benzyloxy)methyl ether
CAS No.:109334-34-1
Molecular Formula:C₂₈H₄₂O₂
Molecular Weight:410.64
Hs Code.:

Synonyms:rel-(1R,2R)-(5E,9E,13E)-2-isopropyl-5,9,13-trimethyl-5,9,13-cyclotetradecatrienyl (benzyloxy)methyl ether

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Chemical Property of rel-(1R,2R)-(5E,9E,13E)-2-isopropyl-5,9,13-trimethyl-5,9,13-cyclotetradecatrienyl (benzyloxy)methyl ether

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Technology Process of rel-(1R,2R)-(5E,9E,13E)-2-isopropyl-5,9,13-trimethyl-5,9,13-cyclotetradecatrienyl (benzyloxy)methyl ether

There total 19 articles about rel-(1R,2R)-(5E,9E,13E)-2-isopropyl-5,9,13-trimethyl-5,9,13-cyclotetradecatrienyl (benzyloxy)methyl ether 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:

: 3587-60-8
Benzyloxymethyl chloride

: 109334-34-1
rel-(1R,2R)-(5E,9E,13E)-2-isopropyl-5,9,13-trimethyl-5,9,13-cyclotetradecatrienyl (benzyloxy)methyl ether

Guidance literature:: Multi-step reaction with 2 steps

1: 65 percent / ethyldiisopropylamine / CH₂Cl₂ / 2.5 h

2: 1.) t-BuLi, 2.) H₂C₅₄H₄₅P₃ClRh / 2.) (Ph₃P)3RhCl / 1) THF, hexane, -78 deg C, 1 h, 2) ethanol, benzene, 4h

With H₂C₅₄H₄₅P₃ClRh; tert.-butyl lithium; N-ethyl-N,N-diisopropylamine; Wilkinson's catalyst; In dichloromethane;
DOI:10.1021/jo00226a026

Reference yield:

: 104465-89-6
(2E,6E,10E)-2,6,10-trimethyl-2,6,10-pentadecatrien-14-yn-1-ol

: 109334-34-1
rel-(1R,2R)-(5E,9E,13E)-2-isopropyl-5,9,13-trimethyl-5,9,13-cyclotetradecatrienyl (benzyloxy)methyl ether

Guidance literature:: Multi-step reaction with 7 steps

1: 0.49 g / LiCl, 2,6-lutidine, methanesulfonyl chloride / dimethylformamide / 7 h

2: n-BuLi / 1) THF, -78 deg C, 1h; 2) THF, from -78 deg C to 20 deg C

3: 71 percent / 1,10-phenanthroline, ethylmagnesium bromide / hexamethylphosphoric acid triamide; tetrahydrofuran / 4 h / Heating

4: 52 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

5: 1.) sodium bis(2-methoxyetoxy)aluminum hydride, 2.) I₂ / 1.) THF, 13.5 h, RT, 2.) THF, -78 deg C, 3 min

6: 65 percent / ethyldiisopropylamine / CH₂Cl₂ / 2.5 h

7: 1.) t-BuLi, 2.) H₂C₅₄H₄₅P₃ClRh / 2.) (Ph₃P)3RhCl / 1) THF, hexane, -78 deg C, 1 h, 2) ethanol, benzene, 4h

With 2,6-dimethylpyridine; n-butyllithium; 1,10-Phenanthroline; H₂C₅₄H₄₅P₃ClRh; ethylmagnesium bromide; iodine; tert.-butyl lithium; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium chloride; Wilkinson's catalyst; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00226a026

Reference yield:

: 4128-17-0
(2E,6E)-farnesyl acetate

: 109334-34-1
rel-(1R,2R)-(5E,9E,13E)-2-isopropyl-5,9,13-trimethyl-5,9,13-cyclotetradecatrienyl (benzyloxy)methyl ether

Guidance literature:: Multi-step reaction with 13 steps

1: 14 percent / t-BuOOH, selenium dioxide / CH₂Cl₂ / 1.5 h / 0 °C

2: triethylamine, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 1 h / Ambient temperature

3: K₂CO₃ / methanol / 3 h / 0 °C

4: 3.67 g / LiCl, 2,6-lutidine, methanesulfonyl chloride / dimethylformamide / 7 h

5: 1.) CuI / 1.) THF, -78 deg C, 30 min, 2.) THF, -20 deg C, 3 h

6: n-Bu₄NF / tetrahydrofuran

7: 0.49 g / LiCl, 2,6-lutidine, methanesulfonyl chloride / dimethylformamide / 7 h

8: n-BuLi / 1) THF, -78 deg C, 1h; 2) THF, from -78 deg C to 20 deg C

9: 71 percent / 1,10-phenanthroline, ethylmagnesium bromide / hexamethylphosphoric acid triamide; tetrahydrofuran / 4 h / Heating

10: 52 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

11: 1.) sodium bis(2-methoxyetoxy)aluminum hydride, 2.) I₂ / 1.) THF, 13.5 h, RT, 2.) THF, -78 deg C, 3 min

12: 65 percent / ethyldiisopropylamine / CH₂Cl₂ / 2.5 h

13: 1.) t-BuLi, 2.) H₂C₅₄H₄₅P₃ClRh / 2.) (Ph₃P)3RhCl / 1) THF, hexane, -78 deg C, 1 h, 2) ethanol, benzene, 4h

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; copper(l) iodide; n-butyllithium; selenium(IV) oxide; 1,10-Phenanthroline; H₂C₅₄H₄₅P₃ClRh; ethylmagnesium bromide; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; potassium carbonate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium chloride; Wilkinson's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00226a026