(2E,4S)-4-[N-benzyl-N-[(2E)-(4-hydroxy-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester

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Chemical Name:(2E,4S)-4-[N-benzyl-N-[(2E)-(4-hydroxy-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester
CAS No.:794518-62-0
Molecular Formula:C₂₅H₄₁NO₄Si
Molecular Weight:447.69
Hs Code.:

Synonyms:(2E,4S)-4-[N-benzyl-N-[(2E)-(4-hydroxy-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester

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Chemical Property of (2E,4S)-4-[N-benzyl-N-[(2E)-(4-hydroxy-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester

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Technology Process of (2E,4S)-4-[N-benzyl-N-[(2E)-(4-hydroxy-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester

There total 9 articles about (2E,4S)-4-[N-benzyl-N-[(2E)-(4-hydroxy-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl 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: 81.0%

: 794518-61-9
(2E,4S)-4-[N-benzyl-N-[(E)-(3-methyl-4-triethylsilyloxy)-2-butenyl]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester

: 794518-62-0
(2E,4S)-4-[N-benzyl-N-[(2E)-(4-hydroxy-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.0833333h;
DOI:10.1021/ol0485666 DOI:10.1002/ejoc.200400824

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 794518-62-0
(2E,4S)-4-[N-benzyl-N-[(2E)-(4-hydroxy-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

2.1: 47 percent / LiBH₄ / tetrahydrofuran; toluene / 0.33 h / 100 °C

3.1: NaHCO₃ / acetonitrile / 0.5 h / 20 °C

3.2: 82 percent / acetonitrile / 3 h / Heating

4.1: (COCl)2; DMSO / CH₂Cl₂ / 0.33 h / -78 °C

4.2: 75 percent / CH₂Cl₂ / 3 h / 25 °C

5.1: 81 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

With dmap; lithium borohydride; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 4.1: Swern oxidation;
DOI:10.1002/ejoc.200400824

Reference yield:

: 123639-56-5,131110-76-4,144001-42-3
methyl (2R)-2-(benzylamino)-3-hydroxypropanoate

: 794518-62-0
(2E,4S)-4-[N-benzyl-N-[(2E)-(4-hydroxy-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / Et₃N; DMAP / CH₂Cl₂ / 12 h / 20 °C

2.1: 47 percent / LiBH₄ / tetrahydrofuran; toluene / 0.33 h / 100 °C

3.1: NaHCO₃ / acetonitrile / 0.5 h / 20 °C

3.2: 82 percent / acetonitrile / 3 h / Heating

4.1: (COCl)2; DMSO / CH₂Cl₂ / 0.33 h / -78 °C

4.2: 75 percent / CH₂Cl₂ / 3 h / 25 °C

5.1: 81 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

With dmap; lithium borohydride; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 4.1: Swern oxidation;
DOI:10.1002/ejoc.200400824