(4S,6R,8S,10S)-11-Benzyloxy-4,6,8,10-tetramethyl-3-triisopropylsilanyloxy-undecanenitrile

Base Information

Chemical Name:(4S,6R,8S,10S)-11-Benzyloxy-4,6,8,10-tetramethyl-3-triisopropylsilanyloxy-undecanenitrile
CAS No.:552298-33-6
Molecular Formula:C₃₁H₅₅NO₂Si
Molecular Weight:501.869
Hs Code.:

Synonyms:(4S,6R,8S,10S)-11-Benzyloxy-4,6,8,10-tetramethyl-3-triisopropylsilanyloxy-undecanenitrile

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Chemical Property of (4S,6R,8S,10S)-11-Benzyloxy-4,6,8,10-tetramethyl-3-triisopropylsilanyloxy-undecanenitrile

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Technology Process of (4S,6R,8S,10S)-11-Benzyloxy-4,6,8,10-tetramethyl-3-triisopropylsilanyloxy-undecanenitrile

There total 14 articles about (4S,6R,8S,10S)-11-Benzyloxy-4,6,8,10-tetramethyl-3-triisopropylsilanyloxy-undecanenitrile 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: 94.0%

: 13154-24-0
triisopropylsilyl chloride

: 552298-32-5
(4S,6R,8S,10S)-11-Benzyloxy-3-hydroxy-4,6,8,10-tetramethyl-undecanenitrile

: 552298-33-6
(4S,6R,8S,10S)-11-Benzyloxy-4,6,8,10-tetramethyl-3-triisopropylsilanyloxy-undecanenitrile

Guidance literature:: With 2,6-dimethylpyridine; dmap; In dichloromethane; at 25 ℃; for 6h;
DOI:10.1021/ol034243i

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 552298-33-6
(4S,6R,8S,10S)-11-Benzyloxy-4,6,8,10-tetramethyl-3-triisopropylsilanyloxy-undecanenitrile

Guidance literature:: Multi-step reaction with 14 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

12.1: 90 percent / n-BuLi / tetrahydrofuran / 1 h / -78 °C

13.1: 96 percent / NaBH₄ / methanol / 1 h

14.1: 94 percent / 2,6-lutidine; DMAP / CH₂Cl₂ / 6 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; 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; methanol; hexane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ol034243i

Reference yield:

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

: 552298-33-6
(4S,6R,8S,10S)-11-Benzyloxy-4,6,8,10-tetramethyl-3-triisopropylsilanyloxy-undecanenitrile

Guidance literature:: Multi-step reaction with 13 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

11.1: 90 percent / n-BuLi / tetrahydrofuran / 1 h / -78 °C

12.1: 96 percent / NaBH₄ / methanol / 1 h

13.1: 94 percent / 2,6-lutidine; DMAP / CH₂Cl₂ / 6 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; n-butyllithium; lithium amidotrihydroborate; tetra(n-butyl)ammonium hydroxide; iodine; diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ol034243i