(2S,3R)-5-[(E)-2-ethoxycarbonylvinyl]-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxybenzo[b]furan

Base Information

• Chemical Name: (2S,3R)-5-[(E)-2-ethoxycarbonylvinyl]-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxybenzo[b]furan
• CAS No.: 352020-02-1
• Molecular Formula: C₂₂H₂₄O₇
• Molecular Weight: 400.428
• Mol file: 352020-02-1.mol

Synonyms:(2S,3R)-5-[(E)-2-ethoxycarbonylvinyl]-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxybenzo[b]furan

Chemical Property of (2S,3R)-5-[(E)-2-ethoxycarbonylvinyl]-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxybenzo[b]furan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-5-[(E)-2-ethoxycarbonylvinyl]-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxybenzo[b]furan

There total 13 articles about (2S,3R)-5-[(E)-2-ethoxycarbonylvinyl]-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxybenzo[b]furan 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:

4-bromoguaiacol (7368-78-7) → (2S,3R)-5-[(E)-2-ethoxycarbonylvinyl]-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxybenzo[b]furan (352020-02-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: K₂CO₃ / acetonitrile / 12 h / Heating

1.2: 94 percent / 6 h / 190 °C

2.1: 81 percent / K₂CO₃ / acetonitrile / 12 h / 20 °C

3.1: aq. OsO₄; NaIO₄ / acetone / 5 h

4.1: 17.0 g / NaClO₂; aq. H₂O₂; NaH₂PO₄ / acetonitrile / 1 h / 10 °C

5.1: (COCl)2 / CH₂Cl₂ / 0 °C

6.1: 95 percent / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7.1: Bu₂BOTf; diisopropylethylamine / CH₂Cl₂ / 4 h / -78 - -15 °C

7.2: CH₂Cl₂ / 1.83 h / -78 - -10 °C

7.3: 86 percent / H₂O₂ / methanol / 1 h / 20 °C

8.1: 95 percent / LiBH₄ / diethyl ether / 5 h / 20 °C

9.1: 77 percent / H₂ / Pd/C / ethyl acetate / 0.75 h / 20 °C / 760 Torr

10.1: 97 percent / imidazole / dimethylformamide / 24 h / 3 °C

11.1: t-BuLi / diethyl ether / 0.5 h / -78 °C

11.2: 91 percent / diethyl ether / 0.17 h / -78 °C

12.1: 81 percent / t-BuOK; dibenzo-18-crown-6 / tetrahydrofuran / 0.5 h / 20 °C

13.1: 94 percent / Bu₄NF / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; lithium borohydride; dibenzo-18-crown-6; n-butyllithium; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; tert.-butyl lithium; potassium carbonate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 1.2: Claisen rearrangement / 7.1: Evans' aldol condensation;

DOI:10.1271/bbb.65.1134

Reference yield:

2-methoxy-phenol (90-05-1) → (2S,3R)-5-[(E)-2-ethoxycarbonylvinyl]-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxybenzo[b]furan (352020-02-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 86 percent / Br₂ / CH₂Cl₂ / -78 - 20 °C

2.1: K₂CO₃ / acetonitrile / 12 h / Heating

2.2: 94 percent / 6 h / 190 °C

3.1: 81 percent / K₂CO₃ / acetonitrile / 12 h / 20 °C

4.1: aq. OsO₄; NaIO₄ / acetone / 5 h

5.1: 17.0 g / NaClO₂; aq. H₂O₂; NaH₂PO₄ / acetonitrile / 1 h / 10 °C

6.1: (COCl)2 / CH₂Cl₂ / 0 °C

7.1: 95 percent / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

8.1: Bu₂BOTf; diisopropylethylamine / CH₂Cl₂ / 4 h / -78 - -15 °C

8.2: CH₂Cl₂ / 1.83 h / -78 - -10 °C

8.3: 86 percent / H₂O₂ / methanol / 1 h / 20 °C

9.1: 95 percent / LiBH₄ / diethyl ether / 5 h / 20 °C

10.1: 77 percent / H₂ / Pd/C / ethyl acetate / 0.75 h / 20 °C / 760 Torr

11.1: 97 percent / imidazole / dimethylformamide / 24 h / 3 °C

12.1: t-BuLi / diethyl ether / 0.5 h / -78 °C

12.2: 91 percent / diethyl ether / 0.17 h / -78 °C

13.1: 81 percent / t-BuOK; dibenzo-18-crown-6 / tetrahydrofuran / 0.5 h / 20 °C

14.1: 94 percent / Bu₄NF / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; lithium borohydride; dibenzo-18-crown-6; n-butyllithium; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; bromine; tert.-butyl lithium; potassium carbonate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 2.2: Claisen rearrangement / 8.1: Evans' aldol condensation;

DOI:10.1271/bbb.65.1134

Reference yield:

2-allyl-4-bromo-6-methoxyphenol (352019-92-2) → (2S,3R)-5-[(E)-2-ethoxycarbonylvinyl]-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxybenzo[b]furan (352020-02-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 81 percent / K₂CO₃ / acetonitrile / 12 h / 20 °C

2.1: aq. OsO₄; NaIO₄ / acetone / 5 h

3.1: 17.0 g / NaClO₂; aq. H₂O₂; NaH₂PO₄ / acetonitrile / 1 h / 10 °C

4.1: (COCl)2 / CH₂Cl₂ / 0 °C

5.1: 95 percent / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

6.1: Bu₂BOTf; diisopropylethylamine / CH₂Cl₂ / 4 h / -78 - -15 °C

6.2: CH₂Cl₂ / 1.83 h / -78 - -10 °C

6.3: 86 percent / H₂O₂ / methanol / 1 h / 20 °C

7.1: 95 percent / LiBH₄ / diethyl ether / 5 h / 20 °C

8.1: 77 percent / H₂ / Pd/C / ethyl acetate / 0.75 h / 20 °C / 760 Torr

9.1: 97 percent / imidazole / dimethylformamide / 24 h / 3 °C

10.1: t-BuLi / diethyl ether / 0.5 h / -78 °C

10.2: 91 percent / diethyl ether / 0.17 h / -78 °C

11.1: 81 percent / t-BuOK; dibenzo-18-crown-6 / tetrahydrofuran / 0.5 h / 20 °C

12.1: 94 percent / Bu₄NF / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; lithium borohydride; dibenzo-18-crown-6; n-butyllithium; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; tert.-butyl lithium; potassium carbonate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 6.1: Evans' aldol condensation;

DOI:10.1271/bbb.65.1134

upstream raw materials:

4-bromoguaiacol

2-methoxy-phenol

2-allyl-4-bromo-6-methoxyphenol

1-allyl-2-benzyloxy-5-bromo-3-methoxybenzene

Downstream raw materials:

(2S,3R)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-5-[(E)-3-hydroxy-1-propenyl]-3-hydroxymethyl-7-methoxybenzo[b]furan

Refernces