isopropyl (3S)-3-((1S)-1-(benzyl(tert-butoxycarbonyl)amino)ethyl)-2,2-dichloropent-4-enethioate

Base Information

• Chemical Name: isopropyl (3S)-3-((1S)-1-(benzyl(tert-butoxycarbonyl)amino)ethyl)-2,2-dichloropent-4-enethioate
• CAS No.: 361341-96-0
• Molecular Formula: C₂₂H₃₁Cl₂NO₃S
• Molecular Weight: 460.465
• Mol file: 361341-96-0.mol

Synonyms:isopropyl (3S)-3-((1S)-1-(benzyl(tert-butoxycarbonyl)amino)ethyl)-2,2-dichloropent-4-enethioate

Chemical Property of isopropyl (3S)-3-((1S)-1-(benzyl(tert-butoxycarbonyl)amino)ethyl)-2,2-dichloropent-4-enethioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of isopropyl (3S)-3-((1S)-1-(benzyl(tert-butoxycarbonyl)amino)ethyl)-2,2-dichloropent-4-enethioate

There total 4 articles about isopropyl (3S)-3-((1S)-1-(benzyl(tert-butoxycarbonyl)amino)ethyl)-2,2-dichloropent-4-enethioate 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: 74.0%

trifluoroacetyl chloride (76-02-8) + tert-butyl N-benzyl-N-[(1S,2E)-4-(isopropylsulfanyl)-1-methyl-2-butenyl]carbamate (361341-93-7) → (4S,5S)-3-benzyl-4-methyl-5-vinyl-1,3-oxazolan-2-one (361342-00-9) + (4S,5R)-3-benzyl-4-methyl-5-vinyl-1,3-oxazolan-2-one + isopropyl (3R)-3-((1S)-1-(benzyl(tert-butoxycarbonyl)amino)ethyl)-2,2-dichloropent-4-enethioate (361341-95-9) + isopropyl (3S)-3-((1S)-1-(benzyl(tert-butoxycarbonyl)amino)ethyl)-2,2-dichloropent-4-enethioate (361341-96-0)

Guidance literature:

With copper; zinc; In diethyl ether; for 4h; Heating;

DOI:10.1016/S0040-4020(01)00465-3

Reference yield:

Methyl (4S,E)-4--2-pentenoate (139190-64-0) → isopropyl (3S)-3-((1S)-1-(benzyl(tert-butoxycarbonyl)amino)ethyl)-2,2-dichloropent-4-enethioate (361341-96-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 75 percent / DIBAL-H / tetrahydrofuran; toluene / 0.5 h / 0 °C

2.1: 71 percent / PPh₃; DEAD / tetrahydrofuran / 0 - 20 °C

3.1: NaOEt / ethanol / 1 h / 20 °C

3.2: 99 percent / ethanol / 12 h

4.1: 17 percent / Zn/Cu / diethyl ether / 4 h / Heating

With sodium ethanolate; copper; diisobutylaluminium hydride; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; ethanol; toluene; 4.1: ketene Claisen rearrangement;

DOI:10.1016/S0040-4020(01)00465-3

Reference yield:

tert-butyl N-benzyl-N-[(1S,2E)-4-hydroxy-1-methyl-2-butenyl]carbamate (361341-91-5) → isopropyl (3S)-3-((1S)-1-(benzyl(tert-butoxycarbonyl)amino)ethyl)-2,2-dichloropent-4-enethioate (361341-96-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 71 percent / PPh₃; DEAD / tetrahydrofuran / 0 - 20 °C

2.1: NaOEt / ethanol / 1 h / 20 °C

2.2: 99 percent / ethanol / 12 h

3.1: 17 percent / Zn/Cu / diethyl ether / 4 h / Heating

With sodium ethanolate; copper; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; ethanol; 3.1: ketene Claisen rearrangement;

DOI:10.1016/S0040-4020(01)00465-3

upstream raw materials:

trifluoroacetyl chloride

tert-butyl N-benzyl-N-[(1S,2E)-4-(isopropylsulfanyl)-1-methyl-2-butenyl]carbamate

Methyl (4S,E)-4--2-pentenoate

tert-butyl N-benzyl-N-[(1S,2E)-4-hydroxy-1-methyl-2-butenyl]carbamate