(2R,3R,αR,α'R,E)-methyl 3-(N-benzyl-N-α-methylbenzylamino)-2-[(N-benzyl-N-α-methylbenzylamino)-methyl]-5-phenyl-pent-4-enoate

Base Information

• Chemical Name: (2R,3R,αR,α'R,E)-methyl 3-(N-benzyl-N-α-methylbenzylamino)-2-[(N-benzyl-N-α-methylbenzylamino)-methyl]-5-phenyl-pent-4-enoate
• CAS No.: 1026773-66-9
• Molecular Formula: C₄₃H₄₆N₂O₂
• Molecular Weight: 622.85
• Mol file: 1026773-66-9.mol

Synonyms:(2R,3R,αR,α'R,E)-methyl 3-(N-benzyl-N-α-methylbenzylamino)-2-[(N-benzyl-N-α-methylbenzylamino)-methyl]-5-phenyl-pent-4-enoate

Chemical Property of (2R,3R,αR,α'R,E)-methyl 3-(N-benzyl-N-α-methylbenzylamino)-2-[(N-benzyl-N-α-methylbenzylamino)-methyl]-5-phenyl-pent-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,αR,α'R,E)-methyl 3-(N-benzyl-N-α-methylbenzylamino)-2-[(N-benzyl-N-α-methylbenzylamino)-methyl]-5-phenyl-pent-4-enoate

There total 3 articles about (2R,3R,αR,α'R,E)-methyl 3-(N-benzyl-N-α-methylbenzylamino)-2-[(N-benzyl-N-α-methylbenzylamino)-methyl]-5-phenyl-pent-4-enoate 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: 8.0%

(R)-N-benzyl-1-phenylethylamine (38235-77-7) + (2E,4E)-methyl 2-acetoxymethyl-5-phenyl-penta-2,4-dienoate (124957-46-6) → (4S,5R,αR,6E)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-7-phenyl-hept-6-enoic acid + (4R,5R,αR,6E)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-7-phenyl-hept-6-enoic acid + (2R,3R,αR,α'R,E)-methyl 3-(N-benzyl-N-α-methylbenzylamino)-2-[(N-benzyl-N-α-methylbenzylamino)-methyl]-5-phenyl-pent-4-enoate (1026773-66-9) + (2S,3R,αR,α'R,E)-methyl 3-(N-benzyl-N-α-methylbenzylamino)-2-[(N-benzyl-N-α-methylbenzylamino)-methyl]-5-phenyl-pent-4-enoate (1026773-63-6)

Guidance literature:

(R)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

(2E,4E)-methyl 2-acetoxymethyl-5-phenyl-penta-2,4-dienoate; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.04.015

Reference yield:

methyl (4E)-3-hydroxy-2-methylene-5-phenylpent-4-enoate (124575-69-5,124957-35-3) → (4R,5R,αR,6E)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-7-phenyl-hept-6-enoic acid + (2R,3R,αR,α'R,E)-methyl 3-(N-benzyl-N-α-methylbenzylamino)-2-[(N-benzyl-N-α-methylbenzylamino)-methyl]-5-phenyl-pent-4-enoate (1026773-66-9) + (2S,3R,αR,α'R,E)-methyl 3-(N-benzyl-N-α-methylbenzylamino)-2-[(N-benzyl-N-α-methylbenzylamino)-methyl]-5-phenyl-pent-4-enoate (1026773-63-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

2.1: N-benzyl-N,N,N-triethylammonium chloride; cesium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

3.3: Inert atmosphere

With n-butyllithium; N-benzyl-N,N,N-triethylammonium chloride; triethylamine; cesium fluoride; In tetrahydrofuran;

DOI:10.1016/j.tetasy.2011.04.015

Reference yield:

(E)-methyl 3-acetoxy-2-methylene-5-phenyl-pent-4-enoate (124957-40-0) → (4R,5R,αR,6E)-4-methoxycarbonyl-5-(N-benzyl-N-α-methylbenzylamino)-7-phenyl-hept-6-enoic acid + (2R,3R,αR,α'R,E)-methyl 3-(N-benzyl-N-α-methylbenzylamino)-2-[(N-benzyl-N-α-methylbenzylamino)-methyl]-5-phenyl-pent-4-enoate (1026773-66-9) + (2S,3R,αR,α'R,E)-methyl 3-(N-benzyl-N-α-methylbenzylamino)-2-[(N-benzyl-N-α-methylbenzylamino)-methyl]-5-phenyl-pent-4-enoate (1026773-63-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-benzyl-N,N,N-triethylammonium chloride; cesium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

2.3: Inert atmosphere

With n-butyllithium; N-benzyl-N,N,N-triethylammonium chloride; cesium fluoride; In tetrahydrofuran;

DOI:10.1016/j.tetasy.2011.04.015

upstream raw materials:

(R)-N-benzyl-1-phenylethylamine

(2E,4E)-methyl 2-acetoxymethyl-5-phenyl-penta-2,4-dienoate

methyl (4E)-3-hydroxy-2-methylene-5-phenylpent-4-enoate

(E)-methyl 3-acetoxy-2-methylene-5-phenyl-pent-4-enoate