(E,4S)-4-[benzyl(tert-butoxycarbonyl)amino]-2-pentenyl ethanethioate

Base Information

• Chemical Name: (E,4S)-4-[benzyl(tert-butoxycarbonyl)amino]-2-pentenyl ethanethioate
• CAS No.: 361341-92-6
• Molecular Formula: C₁₉H₂₇NO₃S
• Molecular Weight: 349.494
• Mol file: 361341-92-6.mol

Synonyms:(E,4S)-4-[benzyl(tert-butoxycarbonyl)amino]-2-pentenyl ethanethioate

Chemical Property of (E,4S)-4-[benzyl(tert-butoxycarbonyl)amino]-2-pentenyl ethanethioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E,4S)-4-[benzyl(tert-butoxycarbonyl)amino]-2-pentenyl ethanethioate

There total 2 articles about (E,4S)-4-[benzyl(tert-butoxycarbonyl)amino]-2-pentenyl ethanethioate 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%

tiolacetic acid (507-09-5) + tert-butyl N-benzyl-N-[(1S,2E)-4-hydroxy-1-methyl-2-butenyl]carbamate (361341-91-5) → (E,4S)-4-[benzyl(tert-butoxycarbonyl)amino]-2-pentenyl ethanethioate (361341-92-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃;

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

Reference yield:

Methyl (4S,E)-4--2-pentenoate (139190-64-0) → (E,4S)-4-[benzyl(tert-butoxycarbonyl)amino]-2-pentenyl ethanethioate (361341-92-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / DIBAL-H / tetrahydrofuran; toluene / 0.5 h / 0 °C

2: 71 percent / PPh₃; DEAD / tetrahydrofuran / 0 - 20 °C

With diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene;

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

Reference yield: 99.0%

isopropyl bromide (75-26-3) + (E,4S)-4-[benzyl(tert-butoxycarbonyl)amino]-2-pentenyl ethanethioate (361341-92-6) → tert-butyl N-benzyl-N-[(1S,2E)-4-(isopropylsulfanyl)-1-methyl-2-butenyl]carbamate (361341-93-7)

Guidance literature:

(E,4S)-4-[benzyl(tert-butoxycarbonyl)amino]-2-pentenyl ethanethioate; With sodium ethanolate; In ethanol; at 20 ℃; for 1h;

isopropyl bromide; In ethanol; for 12h;

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

upstream raw materials:

tiolacetic acid

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

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

Downstream raw materials:

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

N-(benzyl(4-toluenesulfonyl)-(2S,3E)-5-isopropylthio)pent-3-en-2-amine

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

isopropyl (3R)-3-((1S)-1-(benzyl((4-methylphenyl)sulfonyl)amino)ethyl)-2,2-dichloropent-4-enethioate