2α-p-toluenesulfonyloxy-5α-cholestan-6-one

Base Information

• Chemical Name: 2α-p-toluenesulfonyloxy-5α-cholestan-6-one
• CAS No.: 86400-93-3
• Molecular Formula: C₃₄H₅₂O₄S
• Molecular Weight: 556.85
• Mol file: 86400-93-3.mol

Synonyms:

Chemical Property of 2α-p-toluenesulfonyloxy-5α-cholestan-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2α-p-toluenesulfonyloxy-5α-cholestan-6-one

There total 14 articles about 2α-p-toluenesulfonyloxy-5α-cholestan-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: 93.0%

2α-hydroxy-5α-cholestan-6-one (86400-90-0) + p-toluenesulfonyl chloride (98-59-9) → 2α-p-toluenesulfonyloxy-5α-cholestan-6-one (86400-93-3)

Guidance literature:

In pyridine;

DOI:10.1248/cpb.35.986

Reference yield:

cholesterol (57-88-5) → 2α-p-toluenesulfonyloxy-5α-cholestan-6-one (86400-93-3)

Guidance literature:

Multi-step reaction with 14 steps

2: 75 percent / 6 M hydrochloric acid / tetrahydrofuran / 1 h / Ambient temperature

3: 90 percent / pyridine / Ambient temperature

4: 95 percent / lithium bromide / dimethylformamide / 1 h / Heating

5: 17 g / lithium aluminum hydride / tetrahydrofuran / 1 h / Ambient temperature

6: 80 percent / diethylcyclohexylamine / dioxane / 3 h / 50 °C

7: 1.) N-bromosuccinimide; 2.) lithium aluminum hydride / 1.) glyme, water, r.t., 1 h; 2.) THF, reflux, 2 h

8: 3.0 g / Jones reagent / acetone / 0.17 h / Ambient temperature

9: lithium / ethanol; liquid ammonia; tetrahydrofuran / 0.5 h / -78 °C

10: pyridine / Ambient temperature

11: 6 M hydrochloric acid / tetrahydrofuran

12: Jones reagent / acetone

13: 715 mg / 5 percent potassium hydroxide / tetrahydrofuran; methanol / 1 h / Ambient temperature

14: 93 percent / pyridine

With hydrogenchloride; potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; jones reagent; diethyl-cyclohexyl-amine; lithium; lithium bromide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; ammonia; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.35.986

Reference yield:

5α-cholest-2-en-6-one (20281-69-0) → 2α-p-toluenesulfonyloxy-5α-cholestan-6-one (86400-93-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 17 g / lithium aluminum hydride / tetrahydrofuran / 1 h / Ambient temperature

2: 80 percent / diethylcyclohexylamine / dioxane / 3 h / 50 °C

3: 1.) N-bromosuccinimide; 2.) lithium aluminum hydride / 1.) glyme, water, r.t., 1 h; 2.) THF, reflux, 2 h

4: 3.0 g / Jones reagent / acetone / 0.17 h / Ambient temperature

5: lithium / ethanol; liquid ammonia; tetrahydrofuran / 0.5 h / -78 °C

6: pyridine / Ambient temperature

7: 6 M hydrochloric acid / tetrahydrofuran

8: Jones reagent / acetone

9: 715 mg / 5 percent potassium hydroxide / tetrahydrofuran; methanol / 1 h / Ambient temperature

10: 93 percent / pyridine

With hydrogenchloride; potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; jones reagent; diethyl-cyclohexyl-amine; lithium; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; ammonia; acetone;

DOI:10.1248/cpb.35.986

upstream raw materials:

2α-hydroxy-5α-cholestan-6-one

p-toluenesulfonyl chloride

cholesterol

5α-cholest-2-en-6-one

Downstream raw materials:

Toluene-4-sulfonic acid (1R,3aS,3bS,6aS,9S,10aR,10bS,12aR)-1-((R)-1,5-dimethyl-hexyl)-10a,12a-dimethyl-5-oxo-hexadecahydro-6-oxa-benzo[3,4]cyclohepta[1,2-e]inden-9-yl ester

Toluene-4-sulfonic acid (1R,3aS,3bS,6aS,9S,10aR,10bS,12aR)-1-((R)-1,5-dimethyl-hexyl)-10a,12a-dimethyl-6-oxo-hexadecahydro-5-oxa-benzo[3,4]cyclohepta[1,2-e]inden-9-yl ester