(Z)-1,5-diacetoxy-5-[5-benzyloxy-2-(4-methylbenzenesulfonylamino)phenyl]-2-pentene

Base Information

• Chemical Name: (Z)-1,5-diacetoxy-5-[5-benzyloxy-2-(4-methylbenzenesulfonylamino)phenyl]-2-pentene
• CAS No.: 791810-79-2
• Molecular Formula: C₂₉H₃₁NO₇S
• Molecular Weight: 537.634
• Mol file: 791810-79-2.mol

Synonyms:(Z)-1,5-diacetoxy-5-[5-benzyloxy-2-(4-methylbenzenesulfonylamino)phenyl]-2-pentene

Chemical Property of (Z)-1,5-diacetoxy-5-[5-benzyloxy-2-(4-methylbenzenesulfonylamino)phenyl]-2-pentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-1,5-diacetoxy-5-[5-benzyloxy-2-(4-methylbenzenesulfonylamino)phenyl]-2-pentene

There total 10 articles about (Z)-1,5-diacetoxy-5-[5-benzyloxy-2-(4-methylbenzenesulfonylamino)phenyl]-2-pentene 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: 97.0%

acetic anhydride (108-24-7) + N-[4-benzyloxy-2-(1,5-dihydroxy-pent-3-enyl)-phenyl]-4-methyl-benzenesulfonamide (791810-67-8) → (Z)-1,5-diacetoxy-5-[5-benzyloxy-2-(4-methylbenzenesulfonylamino)phenyl]-2-pentene (791810-79-2)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1016/j.tet.2004.08.014

Reference yield:

2-amino-5-hydroxybenzoic acid (394-31-0) → (Z)-1,5-diacetoxy-5-[5-benzyloxy-2-(4-methylbenzenesulfonylamino)phenyl]-2-pentene (791810-79-2)

Guidance literature:

Multi-step reaction with 10 steps

1: SO₂Cl / 4 h / Heating

2: pyridine / 5 h / 20 °C

3: 93.3 percent / NaH / dimethylformamide / 15 h / 0 °C

4: 100 percent / LiBH₄ / tetrahydrofuran / 20 h / Heating

5: 80 percent / pyridinium dichromate / CH₂Cl₂ / 3 h / 20 °C

6: 100 percent / diethyl ether; tetrahydrofuran / 2 h / -10 °C

7: 97.4 percent / Et₃N / CH₂Cl₂ / 0.08 h / 20 °C

8: 85.7 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 5 h / Heating

9: TBAF / tetrahydrofuran / 5 h / 20 °C

10: 97 percent / TsOH / CH₂Cl₂ / 3 h / 0 °C

With pyridine; dipyridinium dichromate; Grubbs catalyst first generation; lithium borohydride; sulfuryl dichloride; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.08.014

Reference yield:

methyl 2-amino-5-hydroxybenzoate (1882-72-0) → (Z)-1,5-diacetoxy-5-[5-benzyloxy-2-(4-methylbenzenesulfonylamino)phenyl]-2-pentene (791810-79-2)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine / 5 h / 20 °C

2: 93.3 percent / NaH / dimethylformamide / 15 h / 0 °C

3: 100 percent / LiBH₄ / tetrahydrofuran / 20 h / Heating

4: 80 percent / pyridinium dichromate / CH₂Cl₂ / 3 h / 20 °C

5: 100 percent / diethyl ether; tetrahydrofuran / 2 h / -10 °C

6: 97.4 percent / Et₃N / CH₂Cl₂ / 0.08 h / 20 °C

7: 85.7 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 5 h / Heating

8: TBAF / tetrahydrofuran / 5 h / 20 °C

9: 97 percent / TsOH / CH₂Cl₂ / 3 h / 0 °C

With pyridine; dipyridinium dichromate; Grubbs catalyst first generation; lithium borohydride; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.08.014

upstream raw materials:

acetic anhydride

N-[4-benzyloxy-2-(1,5-dihydroxy-pent-3-enyl)-phenyl]-4-methyl-benzenesulfonamide

2-amino-5-hydroxybenzoic acid

methyl 2-amino-5-hydroxybenzoate