(2S,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butanoic acid

Base Information

Chemical Name:(2S,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butanoic acid
CAS No.:287929-72-0
Molecular Formula:C₁₈H₂₇NO₄
Molecular Weight:321.417
Hs Code.:

Synonyms:(2S,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butanoic acid

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Chemical Property of (2S,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butanoic acid

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Technology Process of (2S,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butanoic acid

There total 13 articles about (2S,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butanoic 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: 91.0%

: 287929-83-3
(2S,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butan-1-ol

: 287929-72-0
(2S,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butanoic acid

Guidance literature:: With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide; In water; acetone; at 0 ℃; for 2h;
DOI:10.1002/(SICI)1522-2675(20000510)83:5<972::AID-HLCA972>3.0.CO;2-9

Reference yield:

: 487-68-3
mesytaldehyde

: 287929-72-0
(2S,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butanoic acid

Guidance literature:: Multi-step reaction with 11 steps

1: 97 percent / CH₂Cl₂ / 24 h / Heating

2: 86 percent / DIBAL-H / diethyl ether; hexane / 5 h / 20 °C

3: 4 Angstroem mol. sieves; titanium tetraisopropoxide; tert-butyl hydroperoxide / (+)-diisopropyl L-tartrate / CH₂Cl₂; 2,2,4-trimethyl-pentane / 8 h / -30 °C

4: 97 percent / LiClO₄ / acetonitrile / 24 h / 65 °C

5: 68 percent / H₂ / 15 percent Pd(OH)2/C / methanol / 48 h / 20 °C / 760 Torr

6: 91 percent / 1H-imidazole / dimethylformamide / 24 h / 20 °C

7: 82 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / -15 - 20 °C

8: 94 percent / NaH / tetrahydrofuran / 3 h / 20 °C

9: 48 percent / CuI / diethyl ether / 0 °C

10: 86 percent / Bu₄NF*H₂O / tetrahydrofuran / 1 h / 20 °C

11: 91 percent / NaHCO₃; 2,2,6,6-tetramethylpiperidin-1-yloxyl; NaClO / KBr / acetone; H₂O / 2 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium hypochlorite; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; lithium perchlorate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; palladium dihydroxide; L-(+)-diisopropyl tartrate; potassium bromide; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; 1: Condensation / 2: Reduction / 3: Oxidation / 4: Ring cleavage / 5: Hydrogenation / 6: Etherification / 7: Acylation / 8: Elimination / 9: Ring cleavage / 10: Hydrolysis / 11: Oxidation;
DOI:10.1002/(SICI)1522-2675(20000510)83:5<972::AID-HLCA972>3.0.CO;2-9

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 287929-72-0
(2S,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 62 percent / H₂ / 10 percent Pd/C / ethyl acetate / 1 Torr

2: 91 percent / 1H-imidazole / dimethylformamide / 24 h / 20 °C

3: 82 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / -15 - 20 °C

4: 94 percent / NaH / tetrahydrofuran / 3 h / 20 °C

5: 48 percent / CuI / diethyl ether / 0 °C

6: 86 percent / Bu₄NF*H₂O / tetrahydrofuran / 1 h / 20 °C

7: 91 percent / NaHCO₃; 2,2,6,6-tetramethylpiperidin-1-yloxyl; NaClO / KBr / acetone; H₂O / 2 h / 0 °C

With 1H-imidazole; dmap; sodium hypochlorite; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; triethylamine; palladium on activated charcoal; potassium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; 1: Reduction / 2: Etherification / 3: Acylation / 4: Elimination / 5: Ring cleavage / 6: Hydrolysis / 7: Oxidation;
DOI:10.1002/(SICI)1522-2675(20000510)83:5<972::AID-HLCA972>3.0.CO;2-9