(3S,5S)-3-Hydroxy-7-oxa-8-cholesten-6-one

Base Information

• Chemical Name: (3S,5S)-3-Hydroxy-7-oxa-8-cholesten-6-one
• CAS No.: 1262676-25-4
• Molecular Formula: C₂₆H₄₂O₃
• Molecular Weight: 402.618
• Mol file: 1262676-25-4.mol

Synonyms:

Chemical Property of (3S,5S)-3-Hydroxy-7-oxa-8-cholesten-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S)-3-Hydroxy-7-oxa-8-cholesten-6-one

There total 8 articles about (3S,5S)-3-Hydroxy-7-oxa-8-cholesten-6-one 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: 90.0%

(S)-7-Oxa-8-cholesten-3,6-dione (1262676-24-3) → (3S,5S)-3-Hydroxy-7-oxa-8-cholesten-6-one (1262676-25-4)

Guidance literature:

(S)-7-Oxa-8-cholesten-3,6-dione; With sodium tetrahydroborate; In methanol; dichloromethane; at 0 ℃; for 0.333333h;

With ammonium chloride; In methanol; dichloromethane; water;

Reference yield:

7-dehydrocholesterol (434-16-2) → (3S,5S)-3-Hydroxy-7-oxa-8-cholesten-6-one (1262676-25-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 1H-imidazole / dichloromethane / 12 h / 20 °C

2.1: borane-THF / tetrahydrofuran / 0.67 h / 0 - 20 °C

2.2: 1 h / 0 - 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 50 °C

3.2: 20 °C

4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 8 h / 20 °C / Molecular sieve

5.1: sodium periodate; cerium(III) chloride heptahydrate / ruthenium(III) trichloride hydrate / ethyl acetate; acetonitrile; water / 0.67 h / 0 °C

6.1: pyridine; lead(IV) tetraacetate / 0.67 h / 0 °C

7.1: thionyl chloride; triethylamine / dichloromethane / 0.33 h / 20 °C

8.1: sodium tetrahydroborate / dichloromethane; methanol / 0.33 h / 0 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; thionyl chloride; tetrapropylammonium perruthennate; borane-THF; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; lead(IV) tetraacetate; 4-methylmorpholine N-oxide; triethylamine; ruthenium(III) trichloride hydrate; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetonitrile;

Reference yield:

(S)-3-Triethylsiloxy-5,7-cholestadiene (1262677-33-7) → (3S,5S)-3-Hydroxy-7-oxa-8-cholesten-6-one (1262676-25-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: borane-THF / tetrahydrofuran / 0.67 h / 0 - 20 °C

1.2: 1 h / 0 - 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 50 °C

2.2: 20 °C

3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 8 h / 20 °C / Molecular sieve

4.1: sodium periodate; cerium(III) chloride heptahydrate / ruthenium(III) trichloride hydrate / ethyl acetate; acetonitrile; water / 0.67 h / 0 °C

5.1: pyridine; lead(IV) tetraacetate / 0.67 h / 0 °C

6.1: thionyl chloride; triethylamine / dichloromethane / 0.33 h / 20 °C

7.1: sodium tetrahydroborate / dichloromethane; methanol / 0.33 h / 0 °C

With pyridine; sodium tetrahydroborate; sodium periodate; thionyl chloride; tetrapropylammonium perruthennate; borane-THF; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; lead(IV) tetraacetate; 4-methylmorpholine N-oxide; triethylamine; ruthenium(III) trichloride hydrate; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetonitrile;

upstream raw materials:

7-dehydrocholesterol

(S)-7-Oxa-8-cholesten-3,6-dione

(S)-3-Triethylsiloxy-5,7-cholestadiene

(3S, 5S, 6S)-3-Triethylsiloxy-7-cholesten-6-ol