6β-hydroxy-5α-cholest-2-ene

Base Information

• Chemical Name: 6β-hydroxy-5α-cholest-2-ene
• CAS No.: 27948-74-9
• Molecular Formula: C₂₇H₄₆O
• Molecular Weight: 386.662
• Mol file: 27948-74-9.mol

Synonyms:6β-hydroxy-5α-cholest-2-ene

Chemical Property of 6β-hydroxy-5α-cholest-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6β-hydroxy-5α-cholest-2-ene

There total 1 articles about 6β-hydroxy-5α-cholest-2-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:

5α-cholest-2-en-6-one (20281-69-0) → 5α-cholest-2-en-6α-ol (28398-76-7) + 6β-hydroxy-5α-cholest-2-ene (27948-74-9)

Guidance literature:

With potassium borohydride; tetrabutylammomium bromide; In water; at 60 ℃; for 2h; Product distribution; other reagents, polimeric supports;

DOI:10.1016/S0040-4020(97)00011-2

Reference yield:

6β-hydroxy-5α-cholest-2-ene (27948-74-9) → 20-Hydroxyecdysone (5289-74-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 83 percent / p-TsOH*H₂O / CH₂Cl₂ / 0.5 h / 20 °C

2: 80 percent / m-chloroperbenzoic acid; Na₂CO₃ / CH₂Cl₂ / 0.5 h / 20 °C

3: 93 percent / LiAlD₄ / tetrahydrofuran / 0.5 h / 60 °C

4: pyridinium chlorochromate; NaOAc; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.17 h / 20 °C

5: LiAlH₄ / tetrahydrofuran / 0.33 h / 20 °C

6: pyridine / 20 °C

7: 2 N aq. HCl / methanol; tetrahydrofuran / 6 h / 20 °C

8: POCl₃; pyridine / 3 h / 20 °C

9: KOH / methanol; tetrahydrofuran / 20 °C

10: 6.0 mg / hairy roots of Ajuga reptans var. atropurpurea; Tween 80 / acetone; CHCl₃; methanol / Irradiation

With pyridine; hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; lithium aluminium deuteride; Tween 80; 4 A molecular sieve; hairy roots of Ajuga reptans var. atropurpurea; sodium acetate; sodium carbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetone; 1: Etherification / 2: Epoxidation / 3: Reduction / 4: Oxidation / 5: Reduction / 6: Acetylation / 7: deetherification / 8: Dehydration / 9: Deacetylation / 10: hydroxylation;

DOI:10.1248/cpb.48.344

Reference yield:

6β-hydroxy-5α-cholest-2-ene (27948-74-9) → 2β-p-toluenesulfonyloxy-5α-cholestan-6-one (86401-00-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / diethylcyclohexylamine / dioxane / 3 h / 50 °C

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

3: 3.3 g / pyridine / Ambient temperature

4: 6 M hydrochloric caid / tetrahydrofuran / 3 h / 50 °C

5: sodium acetate, pyridinium chlorochromate / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 19 percent / 5 percent potassium hydroxide / tetrahydrofuran; methanol / 1 h / Heating

7: 83 percent / pyridine

With hydrogenchloride; potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; diethyl-cyclohexyl-amine; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane;

DOI:10.1248/cpb.35.986

upstream raw materials:

5α-cholest-2-en-6-one

Downstream raw materials:

Trimethylsilyl-5α-cholest-2-en-6β-ol

20-Hydroxyecdysone

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

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

Refernces

• 1、 Briggs, Josie C.,Hodge, Philip,Zhengpu, Zhang. "Potassium borohydride reductions of immobilised ketosteroids". . p. 3943 - 3956. Retrieved 2007/10/03.