methyl (2S,3S,αR)-2-methyl-3-(N-α-methylbenzylamino)-4-(tert-butyldimethylsilyloxy)butanoate

Base Information

Chemical Name:methyl (2S,3S,αR)-2-methyl-3-(N-α-methylbenzylamino)-4-(tert-butyldimethylsilyloxy)butanoate
CAS No.:944410-89-3
Molecular Formula:C₂₀H₃₅NO₃Si
Molecular Weight:365.588
Hs Code.:

Synonyms:methyl (2S,3S,αR)-2-methyl-3-(N-α-methylbenzylamino)-4-(tert-butyldimethylsilyloxy)butanoate

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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 methyl (2S,3S,αR)-2-methyl-3-(N-α-methylbenzylamino)-4-(tert-butyldimethylsilyloxy)butanoate

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Technology Process of methyl (2S,3S,αR)-2-methyl-3-(N-α-methylbenzylamino)-4-(tert-butyldimethylsilyloxy)butanoate

There total 6 articles about methyl (2S,3S,αR)-2-methyl-3-(N-α-methylbenzylamino)-4-(tert-butyldimethylsilyloxy)butanoate 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: 62.0%

: 944410-83-7
methyl (2S,3S,αR)-2-methyl-3-[N-benzyl-N-(α-methylbenzyl)amino]-4-(tert-butyldimethylsilyloxy)butanoate

: 944410-89-3
methyl (2S,3S,αR)-2-methyl-3-(N-α-methylbenzylamino)-4-(tert-butyldimethylsilyloxy)butanoate

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; at 20 ℃; for 2h;
DOI:10.1016/j.tet.2007.03.026

Reference yield:

: 102191-92-4
tert-butyldimethylsiloxyacetaldehyde

: 944410-89-3
methyl (2S,3S,αR)-2-methyl-3-(N-α-methylbenzylamino)-4-(tert-butyldimethylsilyloxy)butanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 41 percent / LiCl; i-Pr₂NEt / acetonitrile / 48 h / 20 °C

2.1: 60 percent / hexane; tetrahydrofuran / 2 h / -78 °C

3.1: lithium diisopropylamide / tetrahydrofuran / 2 h / -78 °C

3.2: tetrahydrofuran / -78 - 20 °C

4.1: 62 percent / CAN / acetonitrile; H₂O / 2 h / 20 °C

With ammonium cerium(IV) nitrate; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; water; acetonitrile;
DOI:10.1016/j.tet.2007.03.026

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 944410-89-3
methyl (2S,3S,αR)-2-methyl-3-(N-α-methylbenzylamino)-4-(tert-butyldimethylsilyloxy)butanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: imidazole; DMAP / CH₂Cl₂ / 12 h / 20 °C

2.1: O₃ / CH₂Cl₂ / 12 h / -78 °C

2.2: DMS / CH₂Cl₂ / 12 h

3.1: 41 percent / LiCl; i-Pr₂NEt / acetonitrile / 48 h / 20 °C

4.1: 60 percent / hexane; tetrahydrofuran / 2 h / -78 °C

5.1: lithium diisopropylamide / tetrahydrofuran / 2 h / -78 °C

5.2: tetrahydrofuran / -78 - 20 °C

6.1: 62 percent / CAN / acetonitrile; H₂O / 2 h / 20 °C

With 1H-imidazole; dmap; ammonium cerium(IV) nitrate; ozone; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile;
DOI:10.1016/j.tet.2007.03.026