(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
• Mol file: 1193091-46-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

(1R,2R,3r,4S,5S)-2,4-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-ol (96691-93-9) + benzoyl chloride (98-88-4) → (1R,2S,3s,4R,5S)-3-(benzoyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene (1193091-46-1)

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:

(1R,2S,4R,5S)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-one (37081-58-6) → (1R,2S,3s,4R,5S)-3-(benzoyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene (1193091-46-1)

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:

2-chloro-3-pentanone (17042-21-6) → (1R,2S,3s,4R,5S)-3-(benzoyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene (1193091-46-1)

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

upstream raw materials:

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

benzoyl chloride

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

2-chloro-3-pentanone

Downstream raw materials:

((2R,3S,4r,5R,6S)-4-(benzoyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol

(2S,3R,4R,5S,6R)-2-(acetoxymethyl)-6-(hydroxymethyl)-3,5-dimethyl-tetrahydro-2H-pyran-4-yl benzoate