(5Z,8Z,14Z)-(10R,11S,12R)-11,12-Bis-(3,4-dimethoxy-benzyloxy)-10-hydroxy-icosa-5,8,14-trienoic acid methyl ester

Base Information

• Chemical Name: (5Z,8Z,14Z)-(10R,11S,12R)-11,12-Bis-(3,4-dimethoxy-benzyloxy)-10-hydroxy-icosa-5,8,14-trienoic acid methyl ester
• CAS No.: 119119-48-1
• Molecular Formula: C₃₉H₅₆O₉
• Molecular Weight: 668.868

Synonyms:(5Z,8Z,14Z)-(10R,11S,12R)-11,12-Bis-(3,4-dimethoxy-benzyloxy)-10-hydroxy-icosa-5,8,14-trienoic acid methyl ester

Chemical Property of (5Z,8Z,14Z)-(10R,11S,12R)-11,12-Bis-(3,4-dimethoxy-benzyloxy)-10-hydroxy-icosa-5,8,14-trienoic acid methyl ester

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (5Z,8Z,14Z)-(10R,11S,12R)-11,12-Bis-(3,4-dimethoxy-benzyloxy)-10-hydroxy-icosa-5,8,14-trienoic acid methyl ester

There total 12 articles about (5Z,8Z,14Z)-(10R,11S,12R)-11,12-Bis-(3,4-dimethoxy-benzyloxy)-10-hydroxy-icosa-5,8,14-trienoic acid methyl 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:

2-deoxy-D-lyxo-hexopyranose (61-58-5,13299-15-5,13299-16-6,14215-77-1,14215-78-2,20789-85-9,23568-30-1,25494-04-6,34339-39-4,34339-40-7,34339-46-3,34339-47-4,114717-20-3,114717-21-4,137491-75-9,137491-76-0) → (5Z,8Z,14Z)-(10R,11S,12R)-11,12-Bis-(3,4-dimethoxy-benzyloxy)-10-hydroxy-icosa-5,8,14-trienoic acid methyl ester (119119-48-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent

2: DMAP, pyridine / CH₂Cl₂ / 12 h / 40 °C

3: KH / tetrahydrofuran / 3 h / 45 °C

4: ZnBr₂ / CH₂Cl₂; methanol / 12 h / 24 °C

5: 1.) (COCl)2, DMSO; 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h; 2.) -20 deg C, 0.5 h

6: tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -40 - 0 °C

7: AcOH / tetrahydrofuran; H₂O / 3 h / 70 °C

8: 1.) THF, PhCH₃, -78 deg C to O deg C, 2 h; 2.) 0 deg C, 40 min

With pyridine; dmap; oxalyl dichloride; potassium hydride; acetic acid; dimethyl sulfoxide; triethylamine; zinc dibromide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water;

DOI:10.1016/S0040-4039(00)80463-3

Reference yield:

2-deoxy-D-lyxo-hexopyranose (61-58-5,13299-15-5,13299-16-6,14215-77-1,14215-78-2,20789-85-9,23568-30-1,25494-04-6,34339-39-4,34339-40-7,34339-46-3,34339-47-4,114717-20-3,114717-21-4,137491-75-9,137491-76-0) → (5Z,8Z,14E)-(10R,11S,12R)-11,12-Bis-(3,4-dimethoxy-benzyloxy)-10-hydroxy-icosa-5,8,14-trienoic acid methyl ester (119119-48-1,142034-17-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent

2: DMAP, pyridine / CH₂Cl₂ / 12 h / 40 °C

3: KH / tetrahydrofuran / 3 h / 45 °C

4: ZnBr₂ / CH₂Cl₂; methanol / 12 h / 24 °C

5: 1.) (COCl)2, DMSO; 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h; 2.) -20 deg C, 0.5 h

6: tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -40 - 0 °C

7: AcOH / tetrahydrofuran; H₂O / 3 h / 70 °C

8: 1.) THF, PhCH₃, -78 deg C to O deg C, 2 h; 2.) 0 deg C, 40 min

With pyridine; dmap; oxalyl dichloride; potassium hydride; acetic acid; dimethyl sulfoxide; triethylamine; zinc dibromide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water;

DOI:10.1016/S0040-4039(00)80463-3

Reference yield:

(2R,3R,4R)-6-Methoxy-2-trityloxymethyl-tetrahydro-pyran-3,4-diol (132076-70-1) → (5Z,8Z,14Z)-(10R,11S,12R)-11,12-Bis-(3,4-dimethoxy-benzyloxy)-10-hydroxy-icosa-5,8,14-trienoic acid methyl ester (119119-48-1)

Guidance literature:

Multi-step reaction with 6 steps

1: KH / tetrahydrofuran / 3 h / 45 °C

2: ZnBr₂ / CH₂Cl₂; methanol / 12 h / 24 °C

3: 1.) (COCl)2, DMSO; 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h; 2.) -20 deg C, 0.5 h

4: tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -40 - 0 °C

5: AcOH / tetrahydrofuran; H₂O / 3 h / 70 °C

6: 1.) THF, PhCH₃, -78 deg C to O deg C, 2 h; 2.) 0 deg C, 40 min

With oxalyl dichloride; potassium hydride; acetic acid; dimethyl sulfoxide; triethylamine; zinc dibromide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water;

DOI:10.1016/S0040-4039(00)80463-3

upstream raw materials:

2-deoxy-D-lyxo-hexopyranose

(2R,3R,4R)-6-Methoxy-2-trityloxymethyl-tetrahydro-pyran-3,4-diol

[(2R,3R,4R)-3,4-Bis-(3,4-dimethoxy-benzyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-methanol

(2S,3R,4R)-3,4-Bis-(3,4-dimethoxy-benzyloxy)-6-methoxy-tetrahydro-pyran-2-carbaldehyde

Downstream raw materials:

10(S),11(R),12(R)-Trihydroxyeicosa-5(Z),8(Z),14(Z)-Trienoic Acid

Benzoic acid (2E,7Z)-(1S,4S,5R)-4,5-bis-(3,4-dimethoxy-benzyloxy)-1-((Z)-6-methoxycarbonyl-hex-2-enyl)-trideca-2,7-dienyl ester

Benzoic acid (2E,7Z)-(1R,4S,5R)-4,5-bis-(3,4-dimethoxy-benzyloxy)-1-((Z)-6-methoxycarbonyl-hex-2-enyl)-trideca-2,7-dienyl ester

Benzoic acid (2E,7Z)-(1S,4S,5R)-5-acetoxy-4-(3,4-dimethoxy-benzyloxy)-1-((Z)-6-methoxycarbonyl-hex-2-enyl)-trideca-2,7-dienyl ester

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