[2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid

Base Information

Chemical Name:[2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid
CAS No.:864360-90-7
Molecular Formula:C₂₄H₃₉NO₅Si
Molecular Weight:449.663
Hs Code.:

Synonyms:[2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid

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Chemical Property of [2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid

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Technology Process of [2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid

There total 8 articles about [2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic 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:

: 31954-27-5
N-(tert-butoxycarbonyl)glycine methyl ester

: 864360-90-7
[2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: KH / tetrahydrofuran / 1 h / 0 °C

1.2: 90 percent / tetrahydrofuran / 17 h / 0 - 20 °C

2.1: 99 percent / aq. NaOH / tetrahydrofuran / 23 h / 20 °C

3.1: 72 percent / DCC; DMAP / CH₂Cl₂ / 14 h / -30 - 20 °C

4.1: 47 percent / 18-C-6; KH / tetrahydrofuran / 3 h / 20 °C

5.1: 70 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 14 h / 20 °C

7.1: 43 mg / 2-methyl-2-butene; NaClO₂ / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / 20 °C / pH 4

With dmap; sodium hydroxide; sodium chlorite; lithium aluminium tetrahydride; 2-methyl-but-2-ene; 18-crown-6 ether; potassium hydride; Dess-Martin periodane; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl alcohol; 4.1: aza-<2,3>-Wittig sigmatropic rearrangement / 6.1: Dess-Martin oxidation;
DOI:10.1039/b506198a

Reference yield:

: 864360-94-1
[2-(2-tert-butoxy-ethyl)-3-(dimethyl-phenyl-silanyl)-1-formyl-but-3-enyl]-carbamic acid tert-butyl ester

: 864360-90-7
[2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid

Guidance literature:: With sodium chlorite; 2-methyl-but-2-ene; In tetrahydrofuran; tert-butyl alcohol; at 20 ℃; for 2h; pH=4;
DOI:10.1039/b506198a

Reference yield:

: 864360-87-2
[N-tert-butoxycarbonyl-[5-tert-butoxy-2-(dimethylphenylsilanyl)-pent-2-enyl]amino]acetic acid methyl ester

: 864360-90-7
[2S,3R]-2-N-tert-butoxycarbonyl-amino-3-(2-tert-butoxyethyl)-4-(dimethylphenylsilanyl)pent-4-enoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / aq. NaOH / tetrahydrofuran / 23 h / 20 °C

2: 72 percent / DCC; DMAP / CH₂Cl₂ / 14 h / -30 - 20 °C

3: 47 percent / 18-C-6; KH / tetrahydrofuran / 3 h / 20 °C

4: 70 percent / LiAlH₄ / diethyl ether / 1.5 h / 0 °C

5: Dess-Martin periodinane / CH₂Cl₂ / 14 h / 20 °C

6: 43 mg / 2-methyl-2-butene; NaClO₂ / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / 20 °C / pH 4

With dmap; sodium hydroxide; sodium chlorite; lithium aluminium tetrahydride; 2-methyl-but-2-ene; 18-crown-6 ether; potassium hydride; Dess-Martin periodane; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl alcohol; 3: aza-<2,3>-Wittig sigmatropic rearrangement / 5: Dess-Martin oxidation;
DOI:10.1039/b506198a