tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-5-[N'-allyl-N'-3'-(4''-fluorophenoxy)propylamino]pentanoate

Base Information

Chemical Name:tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-5-[N'-allyl-N'-3'-(4''-fluorophenoxy)propylamino]pentanoate
CAS No.:1345718-95-7
Molecular Formula:C₃₆H₄₇FN₂O₄
Molecular Weight:590.779
Hs Code.:

Synonyms:tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-5-[N'-allyl-N'-3'-(4''-fluorophenoxy)propylamino]pentanoate

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Chemical Property of tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-5-[N'-allyl-N'-3'-(4''-fluorophenoxy)propylamino]pentanoate

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Technology Process of tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-5-[N'-allyl-N'-3'-(4''-fluorophenoxy)propylamino]pentanoate

There total 6 articles about tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-5-[N'-allyl-N'-3'-(4''-fluorophenoxy)propylamino]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: 64.0%

: 1345718-94-6
tert-butyl (E)-5-[N-allyl-N-3'-(4''-fluorophenoxy)propylamino]pent-2-enoate

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

: 1345718-95-7
tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-5-[N'-allyl-N'-3'-(4''-fluorophenoxy)propylamino]pentanoate

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

tert-butyl (E)-5-[N-allyl-N-3'-(4''-fluorophenoxy)propylamino]pent-2-enoate; In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;

With (1R)-(?)-(10-camphorsulfonyl)oxaziridine; In tetrahydrofuran; at -78 - 20 ℃; for 16h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2011.12.084

Reference yield: 64.0%

: 1345718-94-6
tert-butyl (E)-5-[N-allyl-N-3'-(4''-fluorophenoxy)propylamino]pent-2-enoate

: lithium benzyl-(R)-1-phenylethylamide

: 1345718-95-7
tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-5-[N'-allyl-N'-3'-(4''-fluorophenoxy)propylamino]pentanoate

Guidance literature:: tert-butyl (E)-5-[N-allyl-N-3'-(4''-fluorophenoxy)propylamino]pent-2-enoate; lithium benzyl-(R)-1-phenylethylamide; In tetrahydrofuran; at -78 ℃; for 2h;

With (1R)-(?)-(10-camphorsulfonyl)oxaziridine; In tetrahydrofuran; at -78 - 20 ℃; for 12h; optical yield given as %de; diastereoselective reaction;
DOI:10.1016/j.tetasy.2011.08.020

Reference yield:

: 401502-00-9
N-(3-(4-fluorophenoxy)propyl)prop-2-en-1-amine

: 1345718-95-7
tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-5-[N'-allyl-N'-3'-(4''-fluorophenoxy)propylamino]pentanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.67 h / -15 °C

2.1: tetrahydrofuran / 16 h / -15 - 20 °C

3.1: tetrahydrofuran / 2 h / -78 °C

3.2: 12 h / -78 - 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; 2.1: Wittig reaction;
DOI:10.1016/j.tetasy.2011.08.020