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

Base Information

• Chemical Name: (4S,6R,8S,10S)-11-Benzyloxy-3-hydroxy-4,6,8,10-tetramethyl-undecanenitrile
• CAS No.: 552298-32-5
• Molecular Formula: C₂₂H₃₅NO₂
• Molecular Weight: 345.525
• Mol file: 552298-32-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (4S,6R,8S,10S)-11-Benzyloxy-3-hydroxy-4,6,8,10-tetramethyl-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: 96.0%

(4S,6R,8S,10S)-11-Benzyloxy-4,6,8,10-tetramethyl-3-oxo-undecanenitrile (552298-31-4) → (4S,6R,8S,10S)-11-Benzyloxy-3-hydroxy-4,6,8,10-tetramethyl-undecanenitrile (552298-32-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 1h;

DOI:10.1021/ol034243i

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (4S,6R,8S,10S)-11-Benzyloxy-3-hydroxy-4,6,8,10-tetramethyl-undecanenitrile (552298-32-5)

Guidance literature:

Multi-step reaction with 13 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

With 1H-imidazole; 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:

(S)-3-benzyloxy-2-methylpropan-1-ol (63930-46-1) → (4S,6R,8S,10S)-11-Benzyloxy-3-hydroxy-4,6,8,10-tetramethyl-undecanenitrile (552298-32-5)

Guidance literature:

Multi-step reaction with 12 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

With 1H-imidazole; 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

upstream raw materials:

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

Benzyloxymethyl chloride

(S)-3-benzyloxy-2-methylpropan-1-ol

(2R)-3-iodo-2-methylpropyl benzyl ether

Downstream raw materials:

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