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

Base Information

Chemical Name:(2E,4S)-4-[N-benzyl-N-[(E)-(3-methyl-4-triethylsilyloxy)-2-butenyl]amino]-5-(tert-butyldimethylsilyloxy)-2-pentenoic acid ethyl ester
CAS No.:794518-61-9
Molecular Formula:C₃₁H₅₅NO₄Si₂
Molecular Weight:561.953
Hs Code.:

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

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

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

There total 11 articles about (2E,4S)-4-[N-benzyl-N-[(E)-(3-methyl-4-triethylsilyloxy)-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: 75.0%

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 794518-60-8
(2S)-2-(benzyl{(2E)-3-methyl-4-[(triethylsilyl)oxy]-2-butenyl}amino)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-propanol

: 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

Guidance literature:: (2S)-2-(benzyl{(2E)-3-methyl-4-[(triethylsilyl)oxy]-2-butenyl}amino)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-propanol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.333333h;

ethyl (triphenylphosphoranylidene)acetate; In dichloromethane; at 25 ℃; for 3h;
DOI:10.1002/ejoc.200400824

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 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

Guidance literature:: Multi-step reaction with 4 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

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