(2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-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-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester
CAS No.:794518-63-1
Molecular Formula:C₂₅H₄₀ClNO₃Si
Molecular Weight:466.136
Hs Code.:

Synonyms:(2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-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-chloro-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-chloro-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-chloro-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: 71.0%

: 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

: 794518-63-1
(2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester

Guidance literature:: (2E,4S)-4-[N-benzyl-N-[(2E)-(4-hydroxy-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester; With methanesulfonyl chloride; triethylamine; In dichloromethane; at -40 ℃; for 1h;

With lithium chloride; In tetrahydrofuran; dichloromethane; at -40 - 20 ℃;
DOI:10.1021/ol0485666

Reference yield:

: 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

: 794518-63-1
(2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 81 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

2.1: MsCl; Et₃N / CH₂Cl₂ / 1 h / -40 °C

2.2: 71 percent / LiCl / tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

With tetrabutyl ammonium fluoride; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.200400824

Reference yield:

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

: 794518-63-1
(2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 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

6.1: MsCl; Et₃N / CH₂Cl₂ / 1 h / -40 °C

6.2: 71 percent / LiCl / tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

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