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

Base Information

Chemical Name:(2S,3S,αS)-tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)-2-fluoropentanoate
CAS No.:1253233-11-2
Molecular Formula:C₃₀H₄₆FNO₃Si
Molecular Weight:515.784
Hs Code.:

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

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Chemical Property of (2S,3S,αS)-tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)-2-fluoropentanoate

Chemical Property:

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Technology Process of (2S,3S,αS)-tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)-2-fluoropentanoate

There total 2 articles about (2S,3S,αS)-tert-butyl 5-(tert-butyldimethylsilyloxy)-3-(N-benzyl-α-methylbenzylamino)-2-fluoropentanoate 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: 62.0%

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

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

: 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:: (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 - -30 ℃; for 3h; Inert atmosphere;

With N-fluoro-4-methyl-N-tosylbenzenesulfonamide; In tetrahydrofuran; hexane; at -50 ℃; for 1h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
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:

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

: 1620398-23-3
C₂₈H₃₅FN₄O₇

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