(S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid (2-cyclohex-1-enyl-ethyl)-amide

Base Information

• Chemical Name: (S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid (2-cyclohex-1-enyl-ethyl)-amide
• CAS No.: 155257-20-8
• Molecular Formula: C₄₀H₆₂N₂O₈
• Molecular Weight: 698.941

Synonyms:(S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid (2-cyclohex-1-enyl-ethyl)-amide

Chemical Property of (S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid (2-cyclohex-1-enyl-ethyl)-amide

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Technology Process of (S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid (2-cyclohex-1-enyl-ethyl)-amide

There total 3 articles about (S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid (2-cyclohex-1-enyl-ethyl)-amide 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: 28.0%

C59H92N2O12 (155257-16-2) → (S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid (2-cyclohex-1-enyl-ethyl)-amide (155257-20-8)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)76509-9

Reference yield:

secorapamycin acid (147438-27-5) → (S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid (2-cyclohex-1-enyl-ethyl)-amide (155257-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 30 percent / DAEC, HOBT, NMM / dimethylformamide / 0 - 25 °C

2: 28 percent / LDA / tetrahydrofuran / -78 °C

With 4-methyl-morpholine; benzotriazol-1-ol; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)76509-9

Reference yield:

2-(1-cyclohexenyl)ethylamine (3399-73-3) → (S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid (2-cyclohex-1-enyl-ethyl)-amide (155257-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 30 percent / DAEC, HOBT, NMM / dimethylformamide / 0 - 25 °C

2: 28 percent / LDA / tetrahydrofuran / -78 °C

With 4-methyl-morpholine; benzotriazol-1-ol; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)76509-9

upstream raw materials:

C₅₉H₉₂N₂O₁₂

secorapamycin acid

2-(1-cyclohexenyl)ethylamine

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