(3S,5S)-2,2,5-trimethyl-9-(methylamino)-9-oxononan-3-yl (2S)-6-((4-methoxy benzyl)oxy)-2-methylhexanoate

Base Information

• Chemical Name: (3S,5S)-2,2,5-trimethyl-9-(methylamino)-9-oxononan-3-yl (2S)-6-((4-methoxy benzyl)oxy)-2-methylhexanoate
• CAS No.: 1385634-72-9
• Molecular Formula: C₂₈H₄₇NO₅
• Molecular Weight: 477.685

Synonyms:(3S,5S)-2,2,5-trimethyl-9-(methylamino)-9-oxononan-3-yl (2S)-6-((4-methoxy benzyl)oxy)-2-methylhexanoate

Chemical Property of (3S,5S)-2,2,5-trimethyl-9-(methylamino)-9-oxononan-3-yl (2S)-6-((4-methoxy benzyl)oxy)-2-methylhexanoate

Chemical Property:

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Technology Process of (3S,5S)-2,2,5-trimethyl-9-(methylamino)-9-oxononan-3-yl (2S)-6-((4-methoxy benzyl)oxy)-2-methylhexanoate

There total 13 articles about (3S,5S)-2,2,5-trimethyl-9-(methylamino)-9-oxononan-3-yl (2S)-6-((4-methoxy benzyl)oxy)-2-methylhexanoate 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: 93.0%

(5S,7S)-7-hydroxy-N,5,8,8-tetramethylnonanamide (1385634-53-6) + (S)-6-((4-methoxybenzyl)oxy)-2-methylhexanoic acid (1385634-65-0) → (3S,5S)-2,2,5-trimethyl-9-(methylamino)-9-oxononan-3-yl (2S)-6-((4-methoxy benzyl)oxy)-2-methylhexanoate (1385634-72-9)

Guidance literature:

(S)-6-((4-methoxybenzyl)oxy)-2-methylhexanoic acid; With 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;

(5S,7S)-7-hydroxy-N,5,8,8-tetramethylnonanamide; With dmap; In tetrahydrofuran; toluene; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jo301121f

Reference yield:

N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-6-((4-methoxybenzyl)oxy)-N-methylhexanamide (1385634-63-8) → (3S,5S)-2,2,5-trimethyl-9-(methylamino)-9-oxononan-3-yl (2S)-6-((4-methoxy benzyl)oxy)-2-methylhexanoate (1385634-72-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium chloride; lithium diisopropyl amide / tetrahydrofuran; hexane / 1.33 h / -78 - 0 °C / Inert atmosphere

1.2: 0.33 h / 0 °C / Inert atmosphere

2.1: sodium hydroxide / methanol; water; tert-butyl alcohol / 85 °C / Inert atmosphere

2.2: pH 3 / Inert atmosphere

3.1: 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

3.2: 12 h / 20 °C / Inert atmosphere

With 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; lithium chloride; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; water; tert-butyl alcohol;

DOI:10.1021/jo301121f

Reference yield:

N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl) (2R)-6-((4-methoxybenzyl)oxy)-N,2-dimethylhexanamide (1385634-64-9) → (3S,5S)-2,2,5-trimethyl-9-(methylamino)-9-oxononan-3-yl (2S)-6-((4-methoxy benzyl)oxy)-2-methylhexanoate (1385634-72-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / methanol; water; tert-butyl alcohol / 85 °C / Inert atmosphere

1.2: pH 3 / Inert atmosphere

2.1: 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

2.2: 12 h / 20 °C / Inert atmosphere

With 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; methanol; water; tert-butyl alcohol;

DOI:10.1021/jo301121f

upstream raw materials:

N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-6-((4-methoxybenzyl)oxy)-N-methylhexanamide

N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl) (2R)-6-((4-methoxybenzyl)oxy)-N,2-dimethylhexanamide

(5S,7S)-7-hydroxy-N,5,8,8-tetramethylnonanamide

(S)-6-((4-methoxybenzyl)oxy)-2-methylhexanoic acid

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