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

Base Information

• Chemical Name: trans-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene
• CAS No.: 143747-02-8
• Molecular Formula: C₂₂H₂₇NO₂
• Molecular Weight: 337.462
• Mol file: 143747-02-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 3 articles about trans-(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:

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester (51987-73-6) → trans-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene (143747-02-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) DIBAL

2: 1.) MsCl, (i-Pr)2NEt, 2.) CuCN

With diisobutylaluminium hydride; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine;

DOI:10.1021/jm00172a002

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) + phenylmagnesium bromide → trans-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene (143747-02-8)

Guidance literature:

With methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; Yield given. Multistep reaction;

DOI:10.1021/jm00172a002

Reference yield:

phenylmagnesium bromide + Methanesulfonic acid 1-((S)-1-tert-butoxycarbonylamino-2-phenyl-ethyl)-allyl ester (144164-48-7) → trans-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene (143747-02-8) + cis-(2S)-2-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenylpent-3-ene (854102-47-9)

Guidance literature:

With 1) CuCN; Yield given. Multistep reaction; 1) THF, ether, -78 deg C to -1 deg C, 2) THF, -70 deg C, 15 min;

DOI:10.1021/jo00047a023

upstream raw materials:

4-<<(tert-butyloxy)carbonyl>amino>-3-hydroxy-5-phenyl-1-pentene

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

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

Downstream raw materials:

[(S)-1-(3-Benzyl-oxiranyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

(3-Azido-1-benzyl-2-hydroxy-4-phenyl-butyl)-carbamic acid tert-butyl ester

(4S,5S,1'S)-4-benzyl-5-<1-<<(tert-butyloxy)carbonyl>amino>-2-phenylethyl>oxazolidin-2-one

(2S,3S,4S)-2-amino-4-<<(tert-butyloxy)carbonyl>amino>-1,5-diphenyl-3-hydroxypentane