ethyl (2E)-4-{benzyl[(2E)-4-chloro-3-methyl-2-butenyl]amino}-5-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenoate

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Chemical Name:ethyl (2E)-4-{benzyl[(2E)-4-chloro-3-methyl-2-butenyl]amino}-5-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenoate
CAS No.:867367-11-1
Molecular Formula:C₃₅H₄₄ClNO₃Si
Molecular Weight:590.278
Hs Code.:

Synonyms:ethyl (2E)-4-{benzyl[(2E)-4-chloro-3-methyl-2-butenyl]amino}-5-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenoate

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Chemical Property of ethyl (2E)-4-{benzyl[(2E)-4-chloro-3-methyl-2-butenyl]amino}-5-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenoate

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Technology Process of ethyl (2E)-4-{benzyl[(2E)-4-chloro-3-methyl-2-butenyl]amino}-5-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenoate

There total 10 articles about ethyl (2E)-4-{benzyl[(2E)-4-chloro-3-methyl-2-butenyl]amino}-5-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenoate 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%

: ethyl (2E)-4-{benzyl[(2E)-4-hydroxy-3-methyl-2-butenyl]amino}-5-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenoate

: 867367-11-1
ethyl (2E)-4-{benzyl[(2E)-4-chloro-3-methyl-2-butenyl]amino}-5-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenoate

Guidance literature:: ethyl (2E)-4-{benzyl[(2E)-4-hydroxy-3-methyl-2-butenyl]amino}-5-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenoate; With methanesulfonyl chloride; triethylamine; In dichloromethane; at -40 ℃; for 1h;

With lithium chloride; In tetrahydrofuran; dichloromethane; at 20 ℃; for 3h;
DOI:10.1002/ejoc.200400824

Reference yield:

: 138777-15-8
ethyl 4-{[tert-butyl(dimethyl)silyl]oxy}-3-methyl-2-butenoate

: 867367-11-1
ethyl (2E)-4-{benzyl[(2E)-4-chloro-3-methyl-2-butenyl]amino}-5-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 96 percent / DIBAL-H / CH₂Cl₂; heptane / 2 h / -78 °C

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

2.2: 8.65 g / LiBr / CH₂Cl₂; tetrahydrofuran / 0 - 20 °C

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

3.2: 84 percent / acetonitrile / 5 h / Heating

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

4.2: 78 percent / CH₂Cl₂ / 3 h / -15 - 25 °C

5.1: 97 percent / PPTS / ethanol / 48 h / 55 °C

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

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

With oxalyl dichloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; In ethanol; n-heptane; dichloromethane; acetonitrile; 4.1: Swern oxidation;
DOI:10.1002/ejoc.200400824

Reference yield:

: 2-(benzylamino)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-propanol

: 867367-11-1
ethyl (2E)-4-{benzyl[(2E)-4-chloro-3-methyl-2-butenyl]amino}-5-{[tert-butyl(diphenyl)silyl]oxy}-2-pentenoate

Guidance literature:: Multi-step reaction with 4 steps

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

1.2: 84 percent / acetonitrile / 5 h / Heating

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

2.2: 78 percent / CH₂Cl₂ / 3 h / -15 - 25 °C

3.1: 97 percent / PPTS / ethanol / 48 h / 55 °C

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

4.2: 71 percent / LiCl / tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

With oxalyl dichloride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; In ethanol; dichloromethane; acetonitrile; 2.1: Swern oxidation;
DOI:10.1002/ejoc.200400824