(S)-1-{2-[(2R,3R,5S,6S)-2-Hydroxy-3,5-dimethyl-6-((S)-1-phenyl-ethyl)-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-1-{2-[(2R,3R,5S,6S)-2-Hydroxy-3,5-dimethyl-6-((S)-1-phenyl-ethyl)-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid tert-butyl ester
• CAS No.: 118143-82-1
• Molecular Formula: C₂₇H₃₉NO₆
• Molecular Weight: 473.61
• Mol file: 118143-82-1.mol

Synonyms:

Chemical Property of (S)-1-{2-[(2R,3R,5S,6S)-2-Hydroxy-3,5-dimethyl-6-((S)-1-phenyl-ethyl)-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-{2-[(2R,3R,5S,6S)-2-Hydroxy-3,5-dimethyl-6-((S)-1-phenyl-ethyl)-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid tert-butyl ester

There total 9 articles about (S)-1-{2-[(2R,3R,5S,6S)-2-Hydroxy-3,5-dimethyl-6-((S)-1-phenyl-ethyl)-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid tert-butyl 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:

tert-butyl (2S)-piperidine-2-carboxylate (118143-76-3) → (S)-1-{2-[(2R,3R,5S,6S)-2-Hydroxy-3,5-dimethyl-6-((S)-1-phenyl-ethyl)-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid tert-butyl ester (118143-82-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / DMAP, pyridine / CH₂Cl₂ / 0 °C

2: 1.) BuLi, TMEDA / 1.) -20 deg C, 2 h, 2.) -78 deg C

3: HF / acetonitrile

4: N-bromosuccinimide / acetone; H₂O

With pyridine; dmap; N-Bromosuccinimide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; hydrogen fluoride; In dichloromethane; water; acetone; acetonitrile;

DOI:10.1021/jo00262a005

Reference yield:

(S)-tert-butyl N-methoxalylpipecolate (118143-77-4) → (S)-1-{2-[(2R,3R,5S,6S)-2-Hydroxy-3,5-dimethyl-6-((S)-1-phenyl-ethyl)-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid tert-butyl ester (118143-82-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) BuLi, TMEDA / 1.) -20 deg C, 2 h, 2.) -78 deg C

2: HF / acetonitrile

3: N-bromosuccinimide / acetone; H₂O

With N-Bromosuccinimide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; hydrogen fluoride; In water; acetone; acetonitrile;

DOI:10.1021/jo00262a005

Reference yield:

C18H28O2 (80160-82-3,118204-93-6) → (S)-1-{2-[(2R,3R,5S,6S)-2-Hydroxy-3,5-dimethyl-6-((S)-1-phenyl-ethyl)-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid tert-butyl ester (118143-82-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) BF₃*OEt₂ / 1.) CH₂Cl₂, from -78 deg C to RT

2: 1.) BuLi, TMEDA / 1.) -20 deg C, 2 h, 2.) -78 deg C

3: HF / acetonitrile

4: N-bromosuccinimide / acetone; H₂O

With N-Bromosuccinimide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; hydrogen fluoride; In water; acetone; acetonitrile;

DOI:10.1021/jo00262a005

upstream raw materials:

(S)-1-{2-[2-(4-Hydroxy-1,3-dimethyl-5-phenyl-hexyl)-[1,3]dithian-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid tert-butyl ester

tert-butyl (2S)-piperidine-2-carboxylate

(S)-tert-butyl N-methoxalylpipecolate

C₁₈H₂₈O₂

Downstream raw materials:

(S)-tert-butyl N-methoxalylpipecolate

(3R,5S,6S)-3,5-Dimethyl-6-((S)-1-phenyl-ethyl)-tetrahydro-pyran-2-one