(tert-butoxycarbonyl)-2(S)-hydroxy-3(S)-amino-5-phenylpentanoic acid methyl ester

Base Information

Chemical Name:(tert-butoxycarbonyl)-2(S)-hydroxy-3(S)-amino-5-phenylpentanoic acid methyl ester
CAS No.:250590-78-4
Molecular Formula:C₁₇H₂₅NO₅
Molecular Weight:323.389
Hs Code.:

Synonyms:(tert-butoxycarbonyl)-2(S)-hydroxy-3(S)-amino-5-phenylpentanoic acid methyl ester

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Chemical Property of (tert-butoxycarbonyl)-2(S)-hydroxy-3(S)-amino-5-phenylpentanoic acid methyl ester

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Technology Process of (tert-butoxycarbonyl)-2(S)-hydroxy-3(S)-amino-5-phenylpentanoic acid methyl ester

There total 7 articles about (tert-butoxycarbonyl)-2(S)-hydroxy-3(S)-amino-5-phenylpentanoic acid methyl ester 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: 52.0%

: 862388-09-8
(3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-5-phenylpentanoic acid

: 18107-18-1
diazomethyl-trimethyl-silane

: 250590-78-4
(tert-butoxycarbonyl)-2(S)-hydroxy-3(S)-amino-5-phenylpentanoic acid methyl ester

: (tert-butoxycarbonyl)-2(R)-hydroxy-3(S)-amino-5-phenylpentanoic acid methyl ester

Guidance literature:: In methanol; hexane; benzene; for 0.333333h;
DOI:10.1016/S0968-0896(99)00127-3

Reference yield:

: C₁₇H₂₃NO₅

: 250590-78-4
(tert-butoxycarbonyl)-2(S)-hydroxy-3(S)-amino-5-phenylpentanoic acid methyl ester

: (tert-butoxycarbonyl)-2(R)-hydroxy-3(S)-amino-5-phenylpentanoic acid methyl ester

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -78 ℃; optical yield given as %ee; Inert atmosphere;
DOI:10.1002/anie.200900701

Reference yield:

: 82732-07-8,108524-68-1,142926-43-0,100564-78-1
Boc-L-homophenylalanine

: 250590-78-4
(tert-butoxycarbonyl)-2(S)-hydroxy-3(S)-amino-5-phenylpentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 50 percent / Et₃N; isobutyl chloroformate / 5 h / 0 °C

2.1: 58 percent / tetrahydrofuran / 4 h / 20 °C

3.1: 90 percent / NaBH₄; CeCl₃*7H₂O / ethanol / 4 h / 0 °C

4.1: methanol / 4 h / -78 °C

4.2: Me₂S / -78 - 20 °C

5.1: 291 mg / 2-methyl-2-buten; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol / 5 h / 20 °C

6.1: 52 percent / benzene; methanol; hexane / 0.33 h

With sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; cerium(III) chloride; 2-methyl-but-2-ene; triethylamine; isobutyl chloroformate; In tetrahydrofuran; methanol; ethanol; hexane; tert-butyl alcohol; benzene; 1.1: Substitution / 2.1: Grignard reaction / 3.1: Reduction / 4.1: ozonolysis / 4.2: Reduction / 5.1: Oxidation / 6.1: Esterification;
DOI:10.1016/S0968-0896(99)00127-3