(3S,4R,αR,E)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-benzyl-N-(α-methyl-4''-methoxybenzyl)-amino]pent-1-ene

Base Information

• Chemical Name: (3S,4R,αR,E)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-benzyl-N-(α-methyl-4''-methoxybenzyl)-amino]pent-1-ene
• CAS No.: 1376622-81-9
• Molecular Formula: C₃₅H₃₉NO₃
• Molecular Weight: 521.7

Synonyms:(3S,4R,αR,E)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-benzyl-N-(α-methyl-4''-methoxybenzyl)-amino]pent-1-ene

Chemical Property of (3S,4R,αR,E)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-benzyl-N-(α-methyl-4''-methoxybenzyl)-amino]pent-1-ene

Chemical Property:

Purity/Quality:

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Technology Process of (3S,4R,αR,E)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-benzyl-N-(α-methyl-4''-methoxybenzyl)-amino]pent-1-ene

There total 4 articles about (3S,4R,αR,E)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-benzyl-N-(α-methyl-4''-methoxybenzyl)-amino]pent-1-ene 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%

C27H31NO3 (1376622-78-4) + (4-methoxybenzyl)triphenylphosphonium bromide (3462-97-3) → (3S,4R,αR,Z)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-benzyl-N-(α-methyl-4''-methoxybenzyl)-amino]pent-1-ene (1376622-84-2) + (3S,4R,αR,E)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-benzyl-N-(α-methyl-4''-methoxybenzyl)-amino]pent-1-ene (1376622-81-9)

Guidance literature:

(4-methoxybenzyl)triphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at 78 ℃; for 0.5h; Inert atmosphere;

C₂₇H₃₁NO₃; In tetrahydrofuran; at -78 - 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.tet.2012.03.045

Reference yield:

tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate (1376622-69-3) → (3S,4R,αR,Z)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-benzyl-N-(α-methyl-4''-methoxybenzyl)-amino]pent-1-ene (1376622-84-2) + (3S,4R,αR,E)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-benzyl-N-(α-methyl-4''-methoxybenzyl)-amino]pent-1-ene (1376622-81-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere

1.2: 12 h / 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 - 20 °C / Inert atmosphere

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

4.2: -78 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; mineral oil; 3.1: Swern oxidation / 3.2: Swern oxidation / 4.2: Wittig reaction;

DOI:10.1016/j.tet.2012.03.045

Reference yield:

tert-butyl (R,R,R)-2-benzyloxy-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate (1376622-72-8) → (3S,4R,αR,Z)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-benzyl-N-(α-methyl-4''-methoxybenzyl)-amino]pent-1-ene (1376622-84-2) + (3S,4R,αR,E)-1-(4'-methoxyphenyl)-3-benzyloxy-4-[N-benzyl-N-(α-methyl-4''-methoxybenzyl)-amino]pent-1-ene (1376622-81-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 - 20 °C / Inert atmosphere

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

3.2: -78 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.2: Wittig reaction;

DOI:10.1016/j.tet.2012.03.045

upstream raw materials:

C₂₇H₃₁NO₃

(4-methoxybenzyl)triphenylphosphonium bromide

tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate

tert-butyl (R,R,R)-2-benzyloxy-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]butanoate

Downstream raw materials:

(R,R,R,R)-N⁽¹⁾-benzyl-2-(4'-methoxyphenyl)-3-iodo-4-benzyloxy-5-methylpyrrolidine

(R,R,R,R)-N⁽¹⁾-benzyl-2-(4'-methoxyphenyl)-3-acetoxy-4-benzyloxy-5-methylpyrrolidine

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