(2S,3S,4R)-4-tert-butoxycarbonylamino-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid

Base Information

Chemical Name:(2S,3S,4R)-4-tert-butoxycarbonylamino-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid
CAS No.:1315271-24-9
Molecular Formula:C₁₈H₂₇NO₅
Molecular Weight:337.416
Hs Code.:

Synonyms:(2S,3S,4R)-4-tert-butoxycarbonylamino-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid

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Chemical Property of (2S,3S,4R)-4-tert-butoxycarbonylamino-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid

Chemical Property:

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Technology Process of (2S,3S,4R)-4-tert-butoxycarbonylamino-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid

There total 4 articles about (2S,3S,4R)-4-tert-butoxycarbonylamino-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid 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:

: 1315271-18-1
(1R,2S,3S,4'S)-[2-hydroxy-1-(2'-methylbenzyl)-4-(4'-isopropyl-2'-oxo-oxazolidin-3'-yl)-3-methyl-4-oxobutyl]carbamic acid tert-butyl ester

: 1315271-24-9
(2S,3S,4R)-4-tert-butoxycarbonylamino-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid

Guidance literature:: (1R,2S,3S,4'S)-[2-hydroxy-1-(2'-methylbenzyl)-4-(4'-isopropyl-2'-oxo-oxazolidin-3'-yl)-3-methyl-4-oxobutyl]carbamic acid tert-butyl ester; With dihydrogen peroxide; lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 3h;

With hydrogenchloride; In water; pH=Ca. 2;
DOI:10.1016/j.bmc.2011.04.047

Reference yield:

: 1315271-13-6
N-(t-butoxycarbonyl)-D-2-methylphenylalaninal

: 1315271-24-9
(2S,3S,4R)-4-tert-butoxycarbonylamino-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 - 0 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

1.3: 4 h / 0 °C

2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 3 h / 0 °C

2.2: pH Ca_. 2

With di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.bmc.2011.04.047

Reference yield:

: 923563-62-6
N-(t-butoxycarbonyl)-D-2-methylphenylalanine N-methyl-N-methoxyamide

: 1315271-24-9
(2S,3S,4R)-4-tert-butoxycarbonylamino-3-hydroxy-2-methyl-5-(2'-methylphenyl)pentanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere

2.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 - 0 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

2.3: 4 h / 0 °C

3.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 3 h / 0 °C

3.2: pH Ca_. 2

With lithium aluminium tetrahydride; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.bmc.2011.04.047