(2R,3R,4R,5S,6S)-7-benzyloxy-2,3-epoxy-5-triethylsilyloxy-4,6-dimethyl-1-heptanol

Base Information

Chemical Name:(2R,3R,4R,5S,6S)-7-benzyloxy-2,3-epoxy-5-triethylsilyloxy-4,6-dimethyl-1-heptanol
CAS No.:155430-45-8
Molecular Formula:C₂₂H₃₈O₄Si
Molecular Weight:394.627
Hs Code.:

Synonyms:(2R,3R,4R,5S,6S)-7-benzyloxy-2,3-epoxy-5-triethylsilyloxy-4,6-dimethyl-1-heptanol

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Chemical Property of (2R,3R,4R,5S,6S)-7-benzyloxy-2,3-epoxy-5-triethylsilyloxy-4,6-dimethyl-1-heptanol

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Technology Process of (2R,3R,4R,5S,6S)-7-benzyloxy-2,3-epoxy-5-triethylsilyloxy-4,6-dimethyl-1-heptanol

There total 11 articles about (2R,3R,4R,5S,6S)-7-benzyloxy-2,3-epoxy-5-triethylsilyloxy-4,6-dimethyl-1-heptanol 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: 99.0%

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

: 155430-45-8
(2R,3R,4R,5S,6S)-7-benzyloxy-2,3-epoxy-5-triethylsilyloxy-4,6-dimethyl-1-heptanol

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0040-4039(98)00804-1

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

: 155430-45-8
(2R,3R,4R,5S,6S)-7-benzyloxy-2,3-epoxy-5-triethylsilyloxy-4,6-dimethyl-1-heptanol

Guidance literature:: Multi-step reaction with 6 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

6.1: 97 percent / mCPBA / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; dmap; oxalyl dichloride; water; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation / 2.2: Wadsworth-Horner-Emmons reaction;
DOI:10.1021/ol035227o

Reference yield:

: 155488-74-7
(E)-(4S,5R,6S)-ethyl 7-benzyloxy-5-hydroxy-4,6-dimethyl-2-heptenoate

: 155430-45-8
(2R,3R,4R,5S,6S)-7-benzyloxy-2,3-epoxy-5-triethylsilyloxy-4,6-dimethyl-1-heptanol

Guidance literature:: Multi-step reaction with 3 steps

1: 22.3 g / DMAP; imidazole / CH₂Cl₂ / 0.5 h / 20 °C

2: 88 percent / DIBAL / tetrahydrofuran; hexane / 0.5 h / 0 °C

3: 97 percent / mCPBA / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; dmap; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol035227o