cis-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene

Base Information

• Chemical Name: cis-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene
• CAS No.: 854102-47-9
• Molecular Formula: C₂₂H₂₇NO₂
• Molecular Weight: 337.462
• Mol file: 854102-47-9.mol

Synonyms:cis-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene

Chemical Property of cis-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene

There total 4 articles about cis-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene 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: 50.0%

Boc-L-phenylalaninal (72155-45-4) + (2-phenylethyl)triphenylphosphonium bromide (53213-26-6) → cis-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene (854102-47-9)

Guidance literature:

(2-phenylethyl)triphenylphosphonium bromide; With potassium hexamethylsilazane; In toluene; at 0 ℃; for 0.25h;

Boc-L-phenylalaninal; In toluene; at 20 ℃; for 20h;

DOI:10.1055/s-2005-861812

Reference yield:

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol (66605-57-0) → cis-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene (854102-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aq. NaOCl; 4-acetamido-2,2,6,6-tetramethylpiperidine-1-yloxy; NaHCO₃ / NaBr / ethyl acetate; toluene / 1 h / -5 °C

2.1: KHMDS / toluene / 0.25 h / 0 °C

2.2: 50 percent / toluene / 20 h / 20 °C

With 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; sodium hypochlorite; potassium hexamethylsilazane; sodium hydrogencarbonate; sodium bromide; In ethyl acetate; toluene; 2.2: Wittig olefination;

DOI:10.1055/s-2005-861812

Reference yield:

4-<<(tert-butyloxy)carbonyl>amino>-3-hydroxy-5-phenyl-1-pentene (99113-28-7,99113-30-1,134806-63-6,139397-08-3,144239-49-6,144239-98-5) → cis-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene (854102-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1: EtN(i-Pr)2 / CH₂Cl₂ / 0.12 h / -10 °C

2: 1) CuCN / 1) THF, ether, -78 deg C to -1 deg C, 2) THF, -70 deg C, 15 min

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo00047a023

upstream raw materials:

Methanesulfonic acid 1-((S)-1-tert-butoxycarbonylamino-2-phenyl-ethyl)-allyl ester

Boc-L-phenylalaninal

(2-phenylethyl)triphenylphosphonium bromide

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol

Downstream raw materials:

[(R)-1-benzyl-3-phenylbutyl]carbamic acid tert-butyl ester