ethyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-4-(tert-butyldimethylsilyloxy)butanoate

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Chemical Name:ethyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-4-(tert-butyldimethylsilyloxy)butanoate
CAS No.:944410-66-6
Molecular Formula:C₂₇H₄₁NO₃Si
Molecular Weight:455.713
Hs Code.:

Synonyms:ethyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-4-(tert-butyldimethylsilyloxy)butanoate

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Chemical Property of ethyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-4-(tert-butyldimethylsilyloxy)butanoate

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Technology Process of ethyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-4-(tert-butyldimethylsilyloxy)butanoate

There total 5 articles about ethyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-4-(tert-butyldimethylsilyloxy)butanoate 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: 72.0%

: lithium benzyl-(R)-1-phenylethylamide

: 94844-37-8
ethyl (2E)-4-{[tert-butyl(dimethyl)silyl]oxy}but-2-enoate

: 944410-66-6
ethyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-4-(tert-butyldimethylsilyloxy)butanoate

Guidance literature:: In tetrahydrofuran; hexane; at -78 ℃; for 2h;
DOI:10.1016/j.tet.2007.03.026

Reference yield:

: 2564-83-2,45842-10-2,126517-51-9,25657-03-8,26933-82-4,54637-06-8,64104-42-3
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

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

: 94844-37-8
ethyl (2E)-4-{[tert-butyl(dimethyl)silyl]oxy}but-2-enoate

: 944410-66-6
ethyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-4-(tert-butyldimethylsilyloxy)butanoate

: (2R,3R)-ethyl 3-[N-benzyl-N-((R)-1-phenylethyl)amino]-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[(2,2,6,6-tetramethylpiperidin-1-yl)oxy]butanoate

: (2S,3R)-ethyl 3-[N-benzyl-N-((R)-1-phenylethyl)amino]-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[(2,2,6,6-tetramethylpiperidin-1-yl)oxy]butanoate

Guidance literature:: (R)-N-benzyl-1-phenylethylamine; With n-butyllithium; lithium chloride; In tetrahydrofuran; hexane; at -78 ℃; for 0.416667h; Inert atmosphere; Schlenk technique;

ethyl (2E)-4-{[tert-butyl(dimethyl)silyl]oxy}but-2-enoate; In tetrahydrofuran; hexane; at -78 ℃; Inert atmosphere; Schlenk technique;

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; With ferrocenium hexafluorophosphate; In tetrahydrofuran; hexane; at -78 ℃; diastereoselective reaction; Inert atmosphere; Schlenk technique;
DOI:10.1002/ejoc.201801139

Reference yield:

: 10080-68-9
(E)-ethyl 4-hydroxybut-2-enoate

: 944410-66-6
ethyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)-amino]-4-(tert-butyldimethylsilyloxy)butanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 3.24 g / Et₃N / CH₂Cl₂ / 55 h / 20 °C

2: 72 percent / hexane; tetrahydrofuran / 2 h / -78 °C

With triethylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/j.tet.2007.03.026