(2R,3S)-1-benzyloxycarbonyl-(3-benzyloxy-2-p-methoxyphenyl)-1,2,3,6-tetrahydropyridine

Base Information

• Chemical Name: (2R,3S)-1-benzyloxycarbonyl-(3-benzyloxy-2-p-methoxyphenyl)-1,2,3,6-tetrahydropyridine
• CAS No.: 914618-57-8
• Molecular Formula: C₂₇H₂₇NO₄
• Molecular Weight: 429.516
• Mol file: 914618-57-8.mol

Synonyms:(2R,3S)-1-benzyloxycarbonyl-(3-benzyloxy-2-p-methoxyphenyl)-1,2,3,6-tetrahydropyridine

Chemical Property of (2R,3S)-1-benzyloxycarbonyl-(3-benzyloxy-2-p-methoxyphenyl)-1,2,3,6-tetrahydropyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-benzyloxycarbonyl-(3-benzyloxy-2-p-methoxyphenyl)-1,2,3,6-tetrahydropyridine

There total 6 articles about (2R,3S)-1-benzyloxycarbonyl-(3-benzyloxy-2-p-methoxyphenyl)-1,2,3,6-tetrahydropyridine 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: 91.0%

(1R,2S)-benzyl N-allyl-N-(2-benzyloxy-1-p-methoxyphenylbut-3-enyl)carbamate (914618-56-7) → (2R,3S)-1-benzyloxycarbonyl-(3-benzyloxy-2-p-methoxyphenyl)-1,2,3,6-tetrahydropyridine (914618-57-8)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1016/j.tetlet.2006.08.040

Reference yield:

(1R,2S)-benzyl N-(2-benzyloxy-1-p-methoxyphenylbut-3-enyl)carbamate (914618-53-4) + allyl bromide (106-95-6) → (2R,3S)-1-benzyloxycarbonyl-(3-benzyloxy-2-p-methoxyphenyl)-1,2,3,6-tetrahydropyridine (914618-57-8)

Guidance literature:

(1R,2S)-benzyl N-(2-benzyloxy-1-p-methoxyphenylbut-3-enyl)carbamate; allyl bromide; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 2h;

Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 4h; Further stages.;

DOI:10.3987/com-07-11066

Reference yield:

(1R,2S)-benzyl N-(2-benzyloxy-1-p-methoxyphenylbut-3-enyl)carbamate (914618-53-4) → (2R,3S)-1-benzyloxycarbonyl-(3-benzyloxy-2-p-methoxyphenyl)-1,2,3,6-tetrahydropyridine (914618-57-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaH / tetrahydrofuran; dimethylformamide; various solvent(s) / 2 h / 20 °C

2: 91 percent / first-generation Grubbs catalyst / CH₂Cl₂ / 4 h / 20 °C

With sodium hydride; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2007.01.028

upstream raw materials:

(1R,2S)-benzyl N-allyl-N-(2-benzyloxy-1-p-methoxyphenylbut-3-enyl)carbamate

(1R,2S)-benzyl N-(2-benzyloxy-1-p-methoxyphenylbut-3-enyl)carbamate

allyl bromide

(1R,2S)-1-(p-methoxyphenyl)but-3-ene-1,2-diol

Downstream raw materials:

(2R,3R,4S,5S)-3-benzyloxy-1-benzyloxycarbonyl-4,5-dihydroxy-2-(p-methoxyphenyl)piperidine

(2R,3S)-1-benzyloxycarbonyl-(3-benzoyloxy-2-hydroxymethyl)piperidine

(2R,3S)-3-benzyloxycarbonyl-2-p-methoxyphenylpiperidine

3-benzoyloxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester