(1R,2S,3s,4R,5S)-3-(benzoyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene

Base Information

Chemical Name:(1R,2S,3s,4R,5S)-3-(benzoyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene
CAS No.:1193091-46-1
Molecular Formula:C₁₆H₁₈O₃
Molecular Weight:258.317
Hs Code.:

Synonyms:(1R,2S,3s,4R,5S)-3-(benzoyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene

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Chemical Property of (1R,2S,3s,4R,5S)-3-(benzoyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene

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Technology Process of (1R,2S,3s,4R,5S)-3-(benzoyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene

There total 3 articles about (1R,2S,3s,4R,5S)-3-(benzoyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene 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: 84.0%

: 96691-93-9
(1R,2R,3r,4S,5S)-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-ol

: 98-88-4
benzoyl chloride

: 1193091-46-1
(1R,2S,3s,4R,5S)-3-(benzoyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene

Guidance literature:: (1R,2R,3r,4S,5S)-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-ol; With potassium hydride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

benzoyl chloride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1021/ol902107g

Reference yield:

: 37081-58-6
(1R,2S,4R,5S)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-one

: 1193091-46-1
(1R,2S,3s,4R,5S)-3-(benzoyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene

Guidance literature:: Multi-step reaction with 2 steps

1.1: methanol; sodium tetrahydroborate / 2 h / 0 °C

2.1: potassium hydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

With methanol; sodium tetrahydroborate; potassium hydride; In tetrahydrofuran;
DOI:10.1002/anie.201308268

Reference yield:

: 17042-21-6
2-chloro-3-pentanone

: 1193091-46-1
(1R,2S,3s,4R,5S)-3-(benzoyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene

Guidance literature:: Multi-step reaction with 3 steps

1.1: triethylamine / water / 12 h / 20 °C

2.1: methanol; sodium tetrahydroborate / 2 h / 0 °C

3.1: potassium hydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

With methanol; sodium tetrahydroborate; potassium hydride; triethylamine; In tetrahydrofuran; water;
DOI:10.1002/anie.201308268