(2E,6E)-(8R,9R)-3-((2S,4R)-2-tert-Butyl-4-methyl-5-oxo-[1,3]dioxolan-4-yl)-9-ethylsulfanylcarbonyl-8-hydroxy-9-(4-methoxy-benzyloxy)-6-methyl-nona-2,6-dienoic acid 2-methoxycarbonyl-ethyl ester

Base Information

• Chemical Name: (2E,6E)-(8R,9R)-3-((2S,4R)-2-tert-Butyl-4-methyl-5-oxo-[1,3]dioxolan-4-yl)-9-ethylsulfanylcarbonyl-8-hydroxy-9-(4-methoxy-benzyloxy)-6-methyl-nona-2,6-dienoic acid 2-methoxycarbonyl-ethyl ester
• CAS No.: 150021-38-8
• Molecular Formula: C₃₃H₄₆O₁₁S
• Molecular Weight: 650.788
• Mol file: 150021-38-8.mol

Synonyms:(2E,6E)-(8R,9R)-3-((2S,4R)-2-tert-Butyl-4-methyl-5-oxo-[1,3]dioxolan-4-yl)-9-ethylsulfanylcarbonyl-8-hydroxy-9-(4-methoxy-benzyloxy)-6-methyl-nona-2,6-dienoic acid 2-methoxycarbonyl-ethyl ester

Chemical Property of (2E,6E)-(8R,9R)-3-((2S,4R)-2-tert-Butyl-4-methyl-5-oxo-[1,3]dioxolan-4-yl)-9-ethylsulfanylcarbonyl-8-hydroxy-9-(4-methoxy-benzyloxy)-6-methyl-nona-2,6-dienoic acid 2-methoxycarbonyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,6E)-(8R,9R)-3-((2S,4R)-2-tert-Butyl-4-methyl-5-oxo-[1,3]dioxolan-4-yl)-9-ethylsulfanylcarbonyl-8-hydroxy-9-(4-methoxy-benzyloxy)-6-methyl-nona-2,6-dienoic acid 2-methoxycarbonyl-ethyl ester

There total 14 articles about (2E,6E)-(8R,9R)-3-((2S,4R)-2-tert-Butyl-4-methyl-5-oxo-[1,3]dioxolan-4-yl)-9-ethylsulfanylcarbonyl-8-hydroxy-9-(4-methoxy-benzyloxy)-6-methyl-nona-2,6-dienoic acid 2-methoxycarbonyl-ethyl 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: 92.0%

[(Z)-1-Ethylsulfanyl-2-(4-methoxy-benzyloxy)-vinyloxy]-trimethyl-silane + (2E,6E)-3-((2S,4R)-2-tert-Butyl-4-methyl-5-oxo-[1,3]dioxolan-4-yl)-6-methyl-8-oxo-octa-2,6-dienoic acid 2-methoxycarbonyl-ethyl ester (150021-37-7) → (2E,6E)-(8R,9R)-3-((2S,4R)-2-tert-Butyl-4-methyl-5-oxo-[1,3]dioxolan-4-yl)-9-ethylsulfanylcarbonyl-8-hydroxy-9-(4-methoxy-benzyloxy)-6-methyl-nona-2,6-dienoic acid 2-methoxycarbonyl-ethyl ester (150021-38-8)

Guidance literature:

With tin(II) trifluoromethanesulfonate; 1-methyl-2-(1-piperidino)pyrrole; n-Bu₂Sn(OAc); In dichloromethane; at -78 ℃; for 18h;

DOI:10.1021/ja00071a066

Reference yield:

(2S,5S)-2-(tert-butyl)-5-methyl-1,3-dioxolan-4-one (81037-07-2,104194-02-7,130930-47-1,146528-25-8,150284-90-5,150284-91-6,81037-06-1) → (2E,6E)-(8R,9R)-3-((2S,4R)-2-tert-Butyl-4-methyl-5-oxo-[1,3]dioxolan-4-yl)-9-ethylsulfanylcarbonyl-8-hydroxy-9-(4-methoxy-benzyloxy)-6-methyl-nona-2,6-dienoic acid 2-methoxycarbonyl-ethyl ester (150021-38-8)

Guidance literature:

Multi-step reaction with 14 steps

1: 69 percent / LDA / tetrahydrofuran / -78 °C

2: Et₃N / diethyl ether / 0.17 h / 0 °C

3: m-chloroperoxybenzoic acid, aq. NaHCO₃ / CH₂Cl₂ / 0.33 h / 0 °C

4: 3N aq. HCl / tetrahydrofuran / 0.25 h / 23 °C

5: H₅IO₆ / tetrahydrofuran / 1.5 h / 23 °C

6: Et₃N / tetrahydrofuran / 2 h / 23 °C

7: 4-dimethylaminopyridine / tetrahydrofuran / 1 h / 23 °C

8: 99 percent / CrO₃, aq. H₂SO₄ / acetone / 0.17 h / 0 °C

9: (COCl)2 / CH₂Cl₂ / 1 h / 23 °C

10: Et₃N / CH₂Cl₂ / 0.33 h / 23 °C

11: 87 percent / PhOH / diethyl ether / 0.33 h / -78 °C

12: Et₃SiH / 10percent Pd/C / acetone / 1 h / 23 °C

13: 1,4-diazabicyclo<2.2.2>octane / CH₂Cl₂ / 2 h / 23 °C

14: 92 percent / (2S)-1-methyl-2-(1-piperidino)pyrrole, Sn(OTf)2, n-Bu₂Sn(OAc) / CH₂Cl₂ / 18 h / -78 °C

With 1,4-diaza-bicyclo[2.2.2]octane; chromium(VI) oxide; hydrogenchloride; triethylsilane; dmap; tin(II) trifluoromethanesulfonate; oxalyl dichloride; 1-methyl-2-(1-piperidino)pyrrole; n-Bu₂Sn(OAc); sulfuric acid; sodium hydrogencarbonate; periodic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; phenol; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;

DOI:10.1021/ja00071a066

Reference yield:

(2S,5R)-2-tert-Butyl-5-methyl-5-(3-oxo-cyclohex-1-enyl)-[1,3]dioxolan-4-one (150021-31-1) → (2E,6E)-(8R,9R)-3-((2S,4R)-2-tert-Butyl-4-methyl-5-oxo-[1,3]dioxolan-4-yl)-9-ethylsulfanylcarbonyl-8-hydroxy-9-(4-methoxy-benzyloxy)-6-methyl-nona-2,6-dienoic acid 2-methoxycarbonyl-ethyl ester (150021-38-8)

Guidance literature:

Multi-step reaction with 13 steps

1: Et₃N / diethyl ether / 0.17 h / 0 °C

2: m-chloroperoxybenzoic acid, aq. NaHCO₃ / CH₂Cl₂ / 0.33 h / 0 °C

3: 3N aq. HCl / tetrahydrofuran / 0.25 h / 23 °C

4: H₅IO₆ / tetrahydrofuran / 1.5 h / 23 °C

5: Et₃N / tetrahydrofuran / 2 h / 23 °C

6: 4-dimethylaminopyridine / tetrahydrofuran / 1 h / 23 °C

7: 99 percent / CrO₃, aq. H₂SO₄ / acetone / 0.17 h / 0 °C

8: (COCl)2 / CH₂Cl₂ / 1 h / 23 °C

9: Et₃N / CH₂Cl₂ / 0.33 h / 23 °C

10: 87 percent / PhOH / diethyl ether / 0.33 h / -78 °C

11: Et₃SiH / 10percent Pd/C / acetone / 1 h / 23 °C

12: 1,4-diazabicyclo<2.2.2>octane / CH₂Cl₂ / 2 h / 23 °C

13: 92 percent / (2S)-1-methyl-2-(1-piperidino)pyrrole, Sn(OTf)2, n-Bu₂Sn(OAc) / CH₂Cl₂ / 18 h / -78 °C

With 1,4-diaza-bicyclo[2.2.2]octane; chromium(VI) oxide; hydrogenchloride; triethylsilane; dmap; tin(II) trifluoromethanesulfonate; oxalyl dichloride; 1-methyl-2-(1-piperidino)pyrrole; n-Bu₂Sn(OAc); sulfuric acid; sodium hydrogencarbonate; periodic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; phenol; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;

DOI:10.1021/ja00071a066

upstream raw materials:

(2E,6E)-3-((2S,4R)-2-tert-Butyl-4-methyl-5-oxo-[1,3]dioxolan-4-yl)-6-methyl-8-oxo-octa-2,6-dienoic acid 2-methoxycarbonyl-ethyl ester

(2S,5S)-2-(tert-butyl)-5-methyl-1,3-dioxolan-4-one

(2S,5R)-2-tert-Butyl-5-methyl-5-(3-oxo-cyclohex-1-enyl)-[1,3]dioxolan-4-one

(E)-3-((2S,4R)-2-tert-Butyl-4-methyl-5-oxo-[1,3]dioxolan-4-yl)-hex-2-enedioic acid 1-(2-methoxycarbonyl-ethyl) ester