methyl (2S,3R,αS)-2-(prop-2′-en-1′-yl)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate

Base Information

Chemical Name:methyl (2S,3R,αS)-2-(prop-2′-en-1′-yl)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate
CAS No.:1596359-36-2
Molecular Formula:C₂₈H₃₁NO₂
Molecular Weight:413.56
Hs Code.:

Synonyms:methyl (2S,3R,αS)-2-(prop-2′-en-1′-yl)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate

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Chemical Property of methyl (2S,3R,αS)-2-(prop-2′-en-1′-yl)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate

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Technology Process of methyl (2S,3R,αS)-2-(prop-2′-en-1′-yl)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate

There total 6 articles about methyl (2S,3R,αS)-2-(prop-2′-en-1′-yl)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate 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:

: 106-95-6
allyl bromide

: 602275-66-1
(R)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-3-phenyl-propionic acid methyl ester

: methyl-2-(prop-2′-en-1′-yl)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate

: 1596359-36-2
methyl (2S,3R,αS)-2-(prop-2′-en-1′-yl)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate

Guidance literature:: (R)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-3-phenyl-propionic acid methyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;

allyl bromide; at 20 ℃; for 16h; Overall yield = 67%; Overall yield = 370 mg; diastereoselective reaction;
DOI:10.1039/c4ob00274a

Reference yield:

: 14990-09-1
tert-butyl cinnamate

: 1596359-36-2
methyl (2S,3R,αS)-2-(prop-2′-en-1′-yl)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

2.1: thionyl chloride / 3 h / 0 - 50 °C / Inert atmosphere

3.1: chloro-trimethyl-silane / toluene / 0.17 h / -78 °C / Inert atmosphere

3.2: 1.5 h / -78 °C / Inert atmosphere

4.1: thionyl chloride / 48 h / 0 - 50 °C / Inert atmosphere

With chloro-trimethyl-silane; thionyl chloride; In tetrahydrofuran; toluene;
DOI:10.1039/c4ob00274a

Reference yield:

: 265669-72-5
tert-butyl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate

: 1596359-36-2
methyl (2S,3R,αS)-2-(prop-2′-en-1′-yl)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: thionyl chloride / 3 h / 0 - 50 °C / Inert atmosphere

2.1: chloro-trimethyl-silane / toluene / 0.17 h / -78 °C / Inert atmosphere

2.2: 1.5 h / -78 °C / Inert atmosphere

3.1: thionyl chloride / 48 h / 0 - 50 °C / Inert atmosphere

With chloro-trimethyl-silane; thionyl chloride; In toluene;
DOI:10.1039/c4ob00274a