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

Base Information

Chemical Name:(E)-3-[(2R,3R)-3-((1S,2S,3S)-4-Benzyloxy-1,3-dimethyl-2-triethylsilanyloxy-butyl)-oxiranyl]-acrylic acid ethyl ester
CAS No.:155430-46-9
Molecular Formula:C₂₆H₄₂O₅Si
Molecular Weight:462.702
Hs Code.:

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

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

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

There total 11 articles about (E)-3-[(2R,3R)-3-((1S,2S,3S)-4-Benzyloxy-1,3-dimethyl-2-triethylsilanyloxy-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:

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

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

Guidance literature:: Multi-step reaction with 8 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

With 1H-imidazole; dmap; oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(97)10782-1

Reference yield:

: 618096-09-6
(2S,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxirane-2-carbaldehyde

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

Guidance literature:: Multi-step reaction with 7 steps

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

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

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

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

5: MCPBA / CH₂Cl₂ / 1 h / -10 °C

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

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

With 1H-imidazole; dmap; oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(97)10782-1

Reference yield:

: 155430-44-7
(E)-(4S,5R,6S)-7-benzyloxy-5-triethylsilyloxy-4,6-dimethyl-2-hepten-1-ol

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

Guidance literature:: Multi-step reaction with 3 steps

1: MCPBA / CH₂Cl₂ / 1 h / -10 °C

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

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

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1016/S0040-4039(97)10782-1