(2S,3S)-1-{[(tert-butyl)dimethylsiyl]oxy}-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butan-2-amine

Base Information

Chemical Name:(2S,3S)-1-{[(tert-butyl)dimethylsiyl]oxy}-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butan-2-amine
CAS No.:287929-82-2
Molecular Formula:C₂₄H₄₃NO₃Si
Molecular Weight:421.696
Hs Code.:

Synonyms:(2S,3S)-1-{[(tert-butyl)dimethylsiyl]oxy}-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butan-2-amine

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Chemical Property of (2S,3S)-1-{[(tert-butyl)dimethylsiyl]oxy}-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butan-2-amine

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Technology Process of (2S,3S)-1-{[(tert-butyl)dimethylsiyl]oxy}-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butan-2-amine

There total 11 articles about (2S,3S)-1-{[(tert-butyl)dimethylsiyl]oxy}-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butan-2-amine 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: 48.0%

: 287929-79-7
(2S)-N-[(tert-butoxy)carbonyl]-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-3-(2,4,6-trimethylphenyl)aziridine

: 74-88-4
methyl iodide

: [3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-1-(2,4,6-trimethyl-phenyl)-propyl]-carbamic acid tert-butyl ester

: 287929-82-2
(2S,3S)-1-{[(tert-butyl)dimethylsiyl]oxy}-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butan-2-amine

Guidance literature:: With copper(l) iodide; In diethyl ether; at 0 ℃;
DOI:10.1002/(SICI)1522-2675(20000510)83:5<972::AID-HLCA972>3.0.CO;2-9

Reference yield:

: 487-68-3
mesytaldehyde

: 287929-82-2
(2S,3S)-1-{[(tert-butyl)dimethylsiyl]oxy}-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butan-2-amine

Guidance literature:: Multi-step reaction with 9 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

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; copper(l) iodide; 4 A molecular sieve; hydrogen; lithium perchlorate; sodium hydride; diisobutylaluminium hydride; triethylamine; palladium dihydroxide; L-(+)-diisopropyl tartrate; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Condensation / 2: Reduction / 3: Oxidation / 4: Ring cleavage / 5: Hydrogenation / 6: Etherification / 7: Acylation / 8: Elimination / 9: Ring cleavage;
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

: 287929-82-2
(2S,3S)-1-{[(tert-butyl)dimethylsiyl]oxy}-2-{[(tert-butoxy)carbonyl]amino}-3-(2,4,6-trimethylphenyl)butan-2-amine

Guidance literature:: Multi-step reaction with 5 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

With 1H-imidazole; dmap; copper(l) iodide; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Reduction / 2: Etherification / 3: Acylation / 4: Elimination / 5: Ring cleavage;
DOI:10.1002/(SICI)1522-2675(20000510)83:5<972::AID-HLCA972>3.0.CO;2-9