Benzoic acid (Z)-(S)-1-formyl-6-methoxycarbonyl-hex-3-enyl ester

Base Information

• Chemical Name: Benzoic acid (Z)-(S)-1-formyl-6-methoxycarbonyl-hex-3-enyl ester
• CAS No.: 853929-41-6
• Molecular Formula: C₁₆H₁₈O₅
• Molecular Weight: 290.316
• Mol file: 853929-41-6.mol

Synonyms:Benzoic acid (Z)-(S)-1-formyl-6-methoxycarbonyl-hex-3-enyl ester

Chemical Property of Benzoic acid (Z)-(S)-1-formyl-6-methoxycarbonyl-hex-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (Z)-(S)-1-formyl-6-methoxycarbonyl-hex-3-enyl ester

There total 6 articles about Benzoic acid (Z)-(S)-1-formyl-6-methoxycarbonyl-hex-3-enyl ester 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: 86.0%

Benzoic acid (Z)-(S)-1-hydroxymethyl-6-methoxycarbonyl-hex-3-enyl ester (853929-38-1) → Benzoic acid (Z)-(S)-1-formyl-6-methoxycarbonyl-hex-3-enyl ester (853929-41-6)

Guidance literature:

With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetlet.2005.03.175

Reference yield:

Benzoic acid (S)-1-benzyloxymethyl-7-hydroxy-hept-3-ynyl ester (853929-30-3) → Benzoic acid (Z)-(S)-1-formyl-6-methoxycarbonyl-hex-3-enyl ester (853929-41-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Jones reagent / acetone / 0 °C

1.2: 93 percent / TMSCl; 2,2-dimethoxypropane / 20 °C

2.1: 98 percent / H₂ / Lindlar cat. / hexane / 20 °C

3.1: 86 percent / EtSH; AlCl₃ / CH₂Cl₂ / -35 °C

4.1: 86 percent / Py*SO₃; DMSO; Et₃N / CH₂Cl₂ / 20 °C

With aluminium trichloride; jones reagent; hydrogen; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; ethanethiol; Lindlar catalyst; In hexane; dichloromethane; acetone; 1.1: Jones oxidation / 4.1: Swern oxidation;

DOI:10.1016/j.tetlet.2005.03.175

Reference yield:

(2S)-1-(benzyloxy)-8-((tetrahydro-2H-pyran-2-yl)oxy)oct-4-yn-2-ol (853929-20-1) → Benzoic acid (Z)-(S)-1-formyl-6-methoxycarbonyl-hex-3-enyl ester (853929-41-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 92 percent / pyridine / 0 - 20 °C

2.1: 88 percent / pyridinium p-toluenesulfonate / methanol / 20 °C

3.1: Jones reagent / acetone / 0 °C

3.2: 93 percent / TMSCl; 2,2-dimethoxypropane / 20 °C

4.1: 98 percent / H₂ / Lindlar cat. / hexane / 20 °C

5.1: 86 percent / EtSH; AlCl₃ / CH₂Cl₂ / -35 °C

6.1: 86 percent / Py*SO₃; DMSO; Et₃N / CH₂Cl₂ / 20 °C

With pyridine; aluminium trichloride; jones reagent; hydrogen; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; ethanethiol; Lindlar catalyst; In methanol; hexane; dichloromethane; acetone; 3.1: Jones oxidation / 6.1: Swern oxidation;

DOI:10.1016/j.tetlet.2005.03.175

upstream raw materials:

Benzoic acid (Z)-(S)-1-hydroxymethyl-6-methoxycarbonyl-hex-3-enyl ester

Benzoic acid (Z)-(S)-1-benzyloxymethyl-6-methoxycarbonyl-hex-3-enyl ester

Benzoic acid (S)-1-benzyloxymethyl-7-hydroxy-hept-3-ynyl ester

(2S)-1-(benzyloxy)-8-((tetrahydro-2H-pyran-2-yl)oxy)oct-4-yn-2-ol

Downstream raw materials:

C₃₇H₃₈O₆

C₃₇H₄₂O₆

7(S),17(S)-resolvin D5

Benzoic acid (Z)-(S)-1-((E)-2-iodo-vinyl)-6-methoxycarbonyl-hex-3-enyl ester