tert-butyl (3R,4R,αS)-3-[N-3',4'-dimethoxybenzyl-N-(α-methylbenzyl)amino]-4-(N,N-dibenzylamino)-5-phenylpentanoate

Base Information

Chemical Name:tert-butyl (3R,4R,αS)-3-[N-3',4'-dimethoxybenzyl-N-(α-methylbenzyl)amino]-4-(N,N-dibenzylamino)-5-phenylpentanoate
CAS No.:1350910-18-7
Molecular Formula:C₄₆H₅₄N₂O₄
Molecular Weight:698.946
Hs Code.:

Synonyms:tert-butyl (3R,4R,αS)-3-[N-3',4'-dimethoxybenzyl-N-(α-methylbenzyl)amino]-4-(N,N-dibenzylamino)-5-phenylpentanoate

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Chemical Property of tert-butyl (3R,4R,αS)-3-[N-3',4'-dimethoxybenzyl-N-(α-methylbenzyl)amino]-4-(N,N-dibenzylamino)-5-phenylpentanoate

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Technology Process of tert-butyl (3R,4R,αS)-3-[N-3',4'-dimethoxybenzyl-N-(α-methylbenzyl)amino]-4-(N,N-dibenzylamino)-5-phenylpentanoate

There total 6 articles about tert-butyl (3R,4R,αS)-3-[N-3',4'-dimethoxybenzyl-N-(α-methylbenzyl)amino]-4-(N,N-dibenzylamino)-5-phenylpentanoate 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: 42.0%

: 1350909-98-6
tert-butyl (RS,E)-4-(N,N-dibenzylamino)-5-phenylpent-2-enoate

: 38235-77-7
(R)-N-benzyl-1-phenylethylamine

: 308273-67-8,680185-65-3
(S)-N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)amine

: 1350910-37-0
tert-butyl (3S,4S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(N,N-dibenzylamino)-5-phenylpentanoate

: 1350910-18-7
tert-butyl (3R,4R,αS)-3-[N-3',4'-dimethoxybenzyl-N-(α-methylbenzyl)amino]-4-(N,N-dibenzylamino)-5-phenylpentanoate

Guidance literature:: (R)-N-benzyl-1-phenylethylamine; (S)-N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)amine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

tert-butyl (RS,E)-4-(N,N-dibenzylamino)-5-phenylpent-2-enoate; In tetrahydrofuran; hexane; at -78 ℃; for 2h; optical yield given as %de; diastereoselective reaction;
DOI:10.1021/ol203011u

Reference yield:

: 150-30-1,25191-15-5,658-69-5,67675-33-6
Phenylalanine

: 1350910-18-7
tert-butyl (3R,4R,αS)-3-[N-3',4'-dimethoxybenzyl-N-(α-methylbenzyl)amino]-4-(N,N-dibenzylamino)-5-phenylpentanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium carbonate / water / 3 h / Reflux

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux

2.2: 0 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

4.1: dichloromethane / 18 h / 20 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: 2 h / -78 °C

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; In tetrahydrofuran; hexane; dichloromethane; water; 3.1: Swern oxidation / 3.2: Swern oxidation / 4.1: Wittig reaction;
DOI:10.1021/ol203011u

Reference yield:

: 180684-58-6
N,N-Dibenzylphenylalanine benzyl ester

: 1350910-18-7
tert-butyl (3R,4R,αS)-3-[N-3',4'-dimethoxybenzyl-N-(α-methylbenzyl)amino]-4-(N,N-dibenzylamino)-5-phenylpentanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux

1.2: 0 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

3.1: dichloromethane / 18 h / 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 2 h / -78 °C

With lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; hexane; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Wittig reaction;
DOI:10.1021/ol203011u