(2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-penten-1-ol

Base Information

Chemical Name:(2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-penten-1-ol
CAS No.:794518-65-3
Molecular Formula:C₂₃H₃₈ClNO₂Si
Molecular Weight:424.099
Hs Code.:

Synonyms:(2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-penten-1-ol

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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-penten-1-ol

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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-penten-1-ol

There total 10 articles about (2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-penten-1-ol 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: 70.0%

: 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

: 794518-65-3
(2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-penten-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 2h;
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

: 794518-65-3
(2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-penten-1-ol

Guidance literature:: Multi-step reaction with 3 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

3.1: 70 percent / DIBAL-H / CH₂Cl₂; hexane / 3 h / -78 °C

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

Reference yield:

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

: 794518-65-3
(2E,4S)-4-[N-benzyl-N-[(2E)-(4-chloro-3-methyl-2-butenyl)]amino]-5-(tert-butyldimethylsilyloxy)-2-penten-1-ol

Guidance literature:: Multi-step reaction with 7 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

7.1: 70 percent / DIBAL-H / CH₂Cl₂; hexane / 3 h / -78 °C

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