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

Base Information

• Chemical Name: ((2R,3S,4r,5R,6S)-4-(benzoyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol
• CAS No.: 1192756-82-3
• Molecular Formula: C₁₆H₂₂O₅
• Molecular Weight: 294.348
• Mol file: 1192756-82-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about ((2R,3S,4r,5R,6S)-4-(benzoyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol 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: 77.0%

(1R,2S,3s,4R,5S)-3-(benzoyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene (1193091-46-1) → ((2R,3S,4r,5R,6S)-4-(benzoyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol (1192756-82-3)

Guidance literature:

(1R,2S,3s,4R,5S)-3-(benzoyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene; With ozone; Sudan III; In methanol; dichloromethane; at -60 ℃;

With sodium tetrahydroborate; In methanol; dichloromethane; at -60 - 0 ℃; Inert atmosphere;

With water; ammonium chloride; In methanol; dichloromethane;

DOI:10.1021/ol902107g

Reference yield:

C16H18O5 → ((2R,3S,4r,5R,6S)-4-(benzoyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol (1192756-82-3)

Guidance literature:

With sodium tetrahydroborate; water; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1002/anie.201308268

Reference yield:

2-chloro-3-pentanone (17042-21-6) → ((2R,3S,4r,5R,6S)-4-(benzoyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2,6-diyl)-dimethanol (1192756-82-3)

Guidance literature:

Multi-step reaction with 5 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

4.1: ozone; dimethylsulfide / dichloromethane / -78 - 20 °C / Inert atmosphere

5.1: sodium tetrahydroborate; water / tetrahydrofuran / 0 - 20 °C

With methanol; sodium tetrahydroborate; dimethylsulfide; water; potassium hydride; ozone; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/anie.201308268

upstream raw materials:

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

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

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

2-chloro-3-pentanone

Downstream raw materials:

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