(E)-3-[(2R,3R)-3-((1R,2S,3S)-4-Benzyloxy-2-hydroxy-1,3-dimethyl-butyl)-oxiranyl]-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-[(2R,3R)-3-((1R,2S,3S)-4-Benzyloxy-2-hydroxy-1,3-dimethyl-butyl)-oxiranyl]-acrylic acid ethyl ester
• CAS No.: 155430-47-0
• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.439
• Mol file: 155430-47-0.mol

Synonyms:(E)-3-[(2R,3R)-3-((1R,2S,3S)-4-Benzyloxy-2-hydroxy-1,3-dimethyl-butyl)-oxiranyl]-acrylic acid ethyl ester

Chemical Property of (E)-3-[(2R,3R)-3-((1R,2S,3S)-4-Benzyloxy-2-hydroxy-1,3-dimethyl-butyl)-oxiranyl]-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[(2R,3R)-3-((1R,2S,3S)-4-Benzyloxy-2-hydroxy-1,3-dimethyl-butyl)-oxiranyl]-acrylic acid ethyl ester

There total 13 articles about (E)-3-[(2R,3R)-3-((1R,2S,3S)-4-Benzyloxy-2-hydroxy-1,3-dimethyl-butyl)-oxiranyl]-acrylic acid 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: 90.0%

(E)-3-[(2R,3R)-3-((1S,2S,3S)-4-Benzyloxy-1,3-dimethyl-2-triethylsilanyloxy-butyl)-oxiranyl]-acrylic acid ethyl ester (155430-46-9) → (E)-3-[(2R,3R)-3-((1R,2S,3S)-4-Benzyloxy-2-hydroxy-1,3-dimethyl-butyl)-oxiranyl]-acrylic acid ethyl ester (155430-47-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(00)73733-6

Reference yield:

(2R,3S,4S)-5-benzyloxy-2,3-epoxy-4-methyl-1-pentanol (73814-75-2,73814-80-9,73837-43-1,79027-31-9,81520-04-9,81520-05-0,81520-09-4,104320-78-7,115458-81-6,115458-82-7,125873-79-2,125873-80-5,81520-08-3) → (E)-3-[(2R,3R)-3-((1R,2S,3S)-4-Benzyloxy-2-hydroxy-1,3-dimethyl-butyl)-oxiranyl]-acrylic acid ethyl ester (155430-47-0)

Guidance literature:

Multi-step reaction with 9 steps

1: (COCl)2/DMSO, Et₃N / CH₂Cl₂ / -78 °C

2: 1.) NaH / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 1.5 h

3: 95 percent / 1,2-dichloro-ethane; H₂O; hexane / -30 °C

4: DMAP, imidazole / dimethylformamide / 2 h / 40 °C

5: i-Bu₂AlH / hexane; CH₂Cl₂ / 1.5 h / -78 °C

6: MCPBA / CH₂Cl₂ / 1 h / -10 °C

7: (COCl)2/DMSO, Et₃N / CH₂Cl₂ / -78 °C

8: 1.) NaH / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 1.5 h

9: TBAF / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)10782-1

Reference yield:

(E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate (155430-43-6) → (E)-3-[(2R,3R)-3-((1R,2S,3S)-4-Benzyloxy-2-hydroxy-1,3-dimethyl-butyl)-oxiranyl]-acrylic acid ethyl ester (155430-47-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / 1,2-dichloro-ethane; H₂O; hexane / -30 °C

2: DMAP, imidazole / dimethylformamide / 2 h / 40 °C

3: i-Bu₂AlH / hexane; CH₂Cl₂ / 1.5 h / -78 °C

4: MCPBA / CH₂Cl₂ / 1 h / -10 °C

5: (COCl)2/DMSO, Et₃N / CH₂Cl₂ / -78 °C

6: 1.) NaH / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 1.5 h

7: TBAF / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)10782-1

upstream raw materials:

(E)-3-[(2R,3R)-3-((1S,2S,3S)-4-Benzyloxy-1,3-dimethyl-2-triethylsilanyloxy-butyl)-oxiranyl]-acrylic acid ethyl ester

(2R,3S,4S)-5-benzyloxy-2,3-epoxy-4-methyl-1-pentanol

(2S,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxirane-2-carbaldehyde

(E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate

Downstream raw materials:

(E)-(4S,5S,6S,7S,8S)-9-Benzyloxy-5,7-dihydroxy-4,6,8-trimethyl-non-2-enoic acid ethyl ester

(S)-4-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pentanal

(3R,4S,7S)-7-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-3-methyl-oct-1-en-4-ol

(2S,3S,4S,5S,6S,9S,10R)-1-Benzyloxy-9-(4-methoxy-benzyloxy)-2,4,6,10-tetramethyl-dodec-11-ene-3,5-diol