(2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ethyl ester

Base Information

Chemical Name:(2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ethyl ester
CAS No.:552298-30-3
Molecular Formula:C₂₂H₃₆O₃
Molecular Weight:348.526
Hs Code.:

Synonyms:(2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ethyl ester

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Chemical Property of (2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ethyl ester

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Technology Process of (2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ethyl ester

There total 11 articles about (2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ethyl ester 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: 95.0%

: 64-17-5
ethanol

: 552298-23-4
(2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid

: 552298-30-3
(2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ethyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 25 ℃; for 2h;
DOI:10.1021/ol034243i

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 552298-30-3
(2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: TiCl₄; iPr₂NEt / CH₂Cl₂ / 6 h / 0 °C

1.2: 68 percent / LiBH₄ / H₂O; tetrahydrofuran / 1 h / 0 °C

2.1: 96 percent / imidazole; I₂; PPh₃ / CH₂Cl₂ / 2 h / 0 °C

3.1: n-BuLi; LiCl; iPr₂NH / hexane; tetrahydrofuran / 1.33 h / -78 - 23 °C

3.2: 97 percent / hexane; tetrahydrofuran / 18.5 h / 0 °C

4.1: 90 percent / n-BuLi; iPr₂NH; LiH₂N*BH₃ / hexane; tetrahydrofuran / 3 h / -78 - 23 °C

5.1: 95 percent / imidazole; I₂; PPh₃ / CH₂Cl₂ / 2 h / 0 °C

6.1: n-BuLi; LiCl; iPr₂NH / hexane; tetrahydrofuran / 1.33 h / -78 - 23 °C

6.2: hexane; tetrahydrofuran / 18.5 h / 0 °C

7.1: 95 percent / n-BuLi; iPr₂NH; LiH₂N*BH₃ / hexane; tetrahydrofuran / 3 h / -78 - 0 °C

8.1: 97 percent / imidazole; I₂; PPh₃ / CH₂Cl₂ / 2 h / 0 °C

9.1: 89 percent / LDA; LiCl / tetrahydrofuran / 18 h / 0 °C

10.1: 84 percent / nBu₄NOH / 2-methyl-propan-2-ol; H₂O / 24 h / Heating

11.1: 95 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 25 °C

With 1H-imidazole; dmap; n-butyllithium; lithium amidotrihydroborate; tetra(n-butyl)ammonium hydroxide; iodine; titanium tetrachloride; diisopropylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ol034243i

Reference yield:

: 63930-46-1
(S)-3-benzyloxy-2-methylpropan-1-ol

: 552298-30-3
(2S,4R,6S,8S)-9-Benzyloxy-2,4,6,8-tetramethyl-nonanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 96 percent / imidazole; I₂; PPh₃ / CH₂Cl₂ / 2 h / 0 °C

2.1: n-BuLi; LiCl; iPr₂NH / hexane; tetrahydrofuran / 1.33 h / -78 - 23 °C

2.2: 97 percent / hexane; tetrahydrofuran / 18.5 h / 0 °C

3.1: 90 percent / n-BuLi; iPr₂NH; LiH₂N*BH₃ / hexane; tetrahydrofuran / 3 h / -78 - 23 °C

4.1: 95 percent / imidazole; I₂; PPh₃ / CH₂Cl₂ / 2 h / 0 °C

5.1: n-BuLi; LiCl; iPr₂NH / hexane; tetrahydrofuran / 1.33 h / -78 - 23 °C

5.2: hexane; tetrahydrofuran / 18.5 h / 0 °C

6.1: 95 percent / n-BuLi; iPr₂NH; LiH₂N*BH₃ / hexane; tetrahydrofuran / 3 h / -78 - 0 °C

7.1: 97 percent / imidazole; I₂; PPh₃ / CH₂Cl₂ / 2 h / 0 °C

8.1: 89 percent / LDA; LiCl / tetrahydrofuran / 18 h / 0 °C

9.1: 84 percent / nBu₄NOH / 2-methyl-propan-2-ol; H₂O / 24 h / Heating

10.1: 95 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 25 °C

With 1H-imidazole; dmap; n-butyllithium; lithium amidotrihydroborate; tetra(n-butyl)ammonium hydroxide; iodine; diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ol034243i