tert-butyl (2R,3S,αR)-2-(2'-methoxy-2'-oxoethyl)-3-[N-allyl-N-(α-methyl-4'''-methoxybenzyl)amino]-3-(2''-N,N-diallylamino-5''-bromophenyl)propanoate

Base Information

Chemical Name:tert-butyl (2R,3S,αR)-2-(2'-methoxy-2'-oxoethyl)-3-[N-allyl-N-(α-methyl-4'''-methoxybenzyl)amino]-3-(2''-N,N-diallylamino-5''-bromophenyl)propanoate
CAS No.:1429058-78-5
Molecular Formula:C₃₄H₄₅BrN₂O₅
Molecular Weight:641.646
Hs Code.:

Synonyms:tert-butyl (2R,3S,αR)-2-(2'-methoxy-2'-oxoethyl)-3-[N-allyl-N-(α-methyl-4'''-methoxybenzyl)amino]-3-(2''-N,N-diallylamino-5''-bromophenyl)propanoate

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Chemical Property of tert-butyl (2R,3S,αR)-2-(2'-methoxy-2'-oxoethyl)-3-[N-allyl-N-(α-methyl-4'''-methoxybenzyl)amino]-3-(2''-N,N-diallylamino-5''-bromophenyl)propanoate

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Technology Process of tert-butyl (2R,3S,αR)-2-(2'-methoxy-2'-oxoethyl)-3-[N-allyl-N-(α-methyl-4'''-methoxybenzyl)amino]-3-(2''-N,N-diallylamino-5''-bromophenyl)propanoate

There total 4 articles about tert-butyl (2R,3S,αR)-2-(2'-methoxy-2'-oxoethyl)-3-[N-allyl-N-(α-methyl-4'''-methoxybenzyl)amino]-3-(2''-N,N-diallylamino-5''-bromophenyl)propanoate 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:

: 1663-39-4,25232-27-3
tert-Butyl acrylate

: 1429058-78-5
tert-butyl (2R,3S,αR)-2-(2'-methoxy-2'-oxoethyl)-3-[N-allyl-N-(α-methyl-4'''-methoxybenzyl)amino]-3-(2''-N,N-diallylamino-5''-bromophenyl)propanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: palladium diacetate; tri-o-tolylphosphine; triethylamine / acetonitrile / 16 h / 70 °C

2.1: potassium phosphate / acetone / 48 h / Reflux

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

3.2: 2 h / -78 °C

4.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C

4.2: 17 h / -78 - 20 °C

With potassium phosphate; n-butyllithium; tri-o-tolylphosphine; palladium diacetate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; acetone; acetonitrile; 1.1: |Heck Reaction;
DOI:10.1021/ol4007508

Reference yield:

: 66416-72-6
4-bromo-2-iodoaniline

: 1429058-78-5
tert-butyl (2R,3S,αR)-2-(2'-methoxy-2'-oxoethyl)-3-[N-allyl-N-(α-methyl-4'''-methoxybenzyl)amino]-3-(2''-N,N-diallylamino-5''-bromophenyl)propanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: palladium diacetate; tri-o-tolylphosphine; triethylamine / acetonitrile / 16 h / 70 °C

2.1: potassium phosphate / acetone / 48 h / Reflux

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

3.2: 2 h / -78 °C

4.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C

4.2: 17 h / -78 - 20 °C

With potassium phosphate; n-butyllithium; tri-o-tolylphosphine; palladium diacetate; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; acetone; acetonitrile; 1.1: |Heck Reaction;
DOI:10.1021/ol4007508

Reference yield:

: 1161719-82-9
(E)-tert-butyl 3-(2-amino-5-bromophenyl)acrylate

: 1429058-78-5
tert-butyl (2R,3S,αR)-2-(2'-methoxy-2'-oxoethyl)-3-[N-allyl-N-(α-methyl-4'''-methoxybenzyl)amino]-3-(2''-N,N-diallylamino-5''-bromophenyl)propanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium phosphate / acetone / 48 h / Reflux

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

2.2: 2 h / -78 °C

3.1: lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C

3.2: 17 h / -78 - 20 °C

With potassium phosphate; n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; hexane; acetone;
DOI:10.1021/ol4007508