(3S,αS)-tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)pentanoate

Base Information

Chemical Name:(3S,αS)-tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)pentanoate
CAS No.:1253232-88-0
Molecular Formula:C₃₀H₄₇NO₃Si
Molecular Weight:497.794
Hs Code.:

Synonyms:(3S,αS)-tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)pentanoate

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Chemical Property of (3S,αS)-tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)pentanoate

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Technology Process of (3S,αS)-tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)pentanoate

There total 1 articles about (3S,αS)-tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)pentanoate 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: 94.0%

: 17480-69-2
(S)-N-benzyl-1-phenylethylamine

: 138877-98-2
(E)-tert-butyl 5-(tert-butyldimethylsilyloxy)pent-2-enoate

: 1253232-88-0
(3S,αS)-tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)pentanoate

Guidance literature:: (S)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

(E)-tert-butyl 5-(tert-butyldimethylsilyloxy)pent-2-enoate; In tetrahydrofuran; hexane; at -78 - -40 ℃; for 3.5h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; hexane; water; at -40 - 0 ℃; optical yield given as %de; diastereoselective reaction;
DOI:10.1021/jo101600c

Reference yield:

: 1253232-88-0
(3S,αS)-tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)pentanoate

: 1253233-11-2
(2S,3S,αS)-tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)-2-fluoropentanoate

: tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)-2-fluoropentanoate

Guidance literature:: (3S,αS)-tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)pentanoate; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

With N-fluoro-4-methyl-N-tosylbenzenesulfonamide; In tetrahydrofuran; hexane; at -78 - -35 ℃; for 4.5h; optical yield given as %de;
DOI:10.1021/jo101600c

Reference yield:

: 1253232-88-0
(3S,αS)-tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)pentanoate

: 1620398-07-3
C₂₈H₃₆N₄O₇

Guidance literature:: Multi-step reaction with 3 steps

1.1: acetic acid; palladium hydroxide, 20 wt% on carbon; hydrogen / methanol; ethyl acetate / 2.5 h / 760.05 Torr

1.2: 1 h

2.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 6 h / 40 °C

3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C

With di-isopropyl azodicarboxylate; palladium hydroxide, 20 wt% on carbon; tetrabutyl ammonium fluoride; hydrogen; acetic acid; triphenylphosphine; In tetrahydrofuran; methanol; ethyl acetate; 3.1: |Mitsunobu Displacement;
DOI:10.1071/CH13590