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

Base Information

Chemical Name:(E)-(4S,5R,6S)-7-benzyloxy-5-triethylsilyloxy-4,6-dimethyl-2-hepten-1-ol
CAS No.:155430-44-7
Molecular Formula:C₂₂H₃₈O₃Si
Molecular Weight:378.627
Hs Code.:

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

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Chemical Property of (E)-(4S,5R,6S)-7-benzyloxy-5-triethylsilyloxy-4,6-dimethyl-2-hepten-1-ol

Chemical Property:

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Technology Process of (E)-(4S,5R,6S)-7-benzyloxy-5-triethylsilyloxy-4,6-dimethyl-2-hepten-1-ol

There total 9 articles about (E)-(4S,5R,6S)-7-benzyloxy-5-triethylsilyloxy-4,6-dimethyl-2-hepten-1-ol 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

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

Guidance literature:: Multi-step reaction with 5 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

2.2: 17.4 g / tetrahydrofuran / 0.5 h / 0 °C

3.1: H₂O / CH₂Cl₂; hexane / 2 h / -30 °C

4.1: 22.3 g / DMAP; imidazole / CH₂Cl₂ / 0.5 h / 20 °C

5.1: 88 percent / DIBAL / tetrahydrofuran; hexane / 0.5 h / 0 °C

With 1H-imidazole; dmap; oxalyl dichloride; water; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation / 2.2: Wadsworth-Horner-Emmons reaction;
DOI:10.1021/ol035227o

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

1.2: 17.4 g / tetrahydrofuran / 0.5 h / 0 °C

2.1: H₂O / CH₂Cl₂; hexane / 2 h / -30 °C

3.1: 22.3 g / DMAP; imidazole / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 88 percent / DIBAL / tetrahydrofuran; hexane / 0.5 h / 0 °C

With 1H-imidazole; dmap; water; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; 1.2: Wadsworth-Horner-Emmons reaction;
DOI:10.1021/ol035227o

Reference yield:

: 155430-43-6
(E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate

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

Guidance literature:: Multi-step reaction with 3 steps

1: H₂O / CH₂Cl₂; hexane / 2 h / -30 °C

2: 22.3 g / DMAP; imidazole / CH₂Cl₂ / 0.5 h / 20 °C

3: 88 percent / DIBAL / tetrahydrofuran; hexane / 0.5 h / 0 °C

With 1H-imidazole; dmap; water; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol035227o