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

Base Information

Chemical Name:(2S,3S,4R)-4-tert-butoxycarbonylamino-3-hydroxy-2-methyl-5-phenyl-pentanoic acid
CAS No.:574012-08-1
Molecular Formula:C₁₇H₂₅NO₅
Molecular Weight:323.389
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

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

There total 4 articles about (2S,3S,4R)-4-tert-butoxycarbonylamino-3-hydroxy-2-methyl-5-phenyl-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: 87.0%

: 574012-06-9
(1R,2S,3S,4'S)-[1-benzyl-2-hydroxy-4-(4'-isopropyl-2'-oxo-oxazolidin-3'-yl)-3-methyl-4-oxobutyl]carbamic acid tert-butyl ester

: 574012-08-1
(2S,3S,4R)-4-tert-butoxycarbonylamino-3-hydroxy-2-methyl-5-phenyl-pentanoic acid

Guidance literature:: With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃; for 3h;
DOI:10.1021/ja021388w

Reference yield:

: 77119-85-8
N-(tert-butoxycarbonyl)-D-phenylalaninal

: 574012-08-1
(2S,3S,4R)-4-tert-butoxycarbonylamino-3-hydroxy-2-methyl-5-phenyl-pentanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: Bu₂BOTf; iPr₂NEt / CH₂Cl₂ / 1 h

1.2: CH₂Cl₂ / -78 - 20 °C

1.3: 3.7 g / aq. H₂O₂ / methanol / 4 h

2.1: 87 percent / aq. H₂O₂; aq. LiOH / tetrahydrofuran / 3 h / 0 °C

With lithium hydroxide; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja021388w

Reference yield:

: 18942-49-9
Boc-D-Phe-OH

: 574012-08-1
(2S,3S,4R)-4-tert-butoxycarbonylamino-3-hydroxy-2-methyl-5-phenyl-pentanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / Inert atmosphere

1.2: Inert atmosphere

1.3: Inert atmosphere

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

3.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / -78 °C / Inert atmosphere

4.1: HLiO₂ / tetrahydrofuran; water / 0 °C

With lithium aluminium tetrahydride; di-n-butylboryl trifluoromethanesulfonate; HLiO₂; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.bmc.2011.04.047