4a-[(4-benzoylphenyl)acetoxy]-6α,7β-diacetoxy-23-[tris(1-methylethyl)]silyloxy-5α-24-norcholane

Base Information

• Chemical Name: 4a-[(4-benzoylphenyl)acetoxy]-6α,7β-diacetoxy-23-[tris(1-methylethyl)]silyloxy-5α-24-norcholane
• CAS No.: 251906-74-8
• Molecular Formula: C₅₁H₇₄O₈Si
• Molecular Weight: 843.229
• Mol file: 251906-74-8.mol

Synonyms:4a-[(4-benzoylphenyl)acetoxy]-6α,7β-diacetoxy-23-[tris(1-methylethyl)]silyloxy-5α-24-norcholane

Chemical Property of 4a-[(4-benzoylphenyl)acetoxy]-6α,7β-diacetoxy-23-[tris(1-methylethyl)]silyloxy-5α-24-norcholane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4a-[(4-benzoylphenyl)acetoxy]-6α,7β-diacetoxy-23-[tris(1-methylethyl)]silyloxy-5α-24-norcholane

There total 12 articles about 4a-[(4-benzoylphenyl)acetoxy]-6α,7β-diacetoxy-23-[tris(1-methylethyl)]silyloxy-5α-24-norcholane 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: 74.0%

(4-benzoylphenyl)acetic acid (26077-80-5) + 6α,7β-diacetoxy-23-[tris(1-methylethyl)]silyloxy-5α-24-norcholan-3β-ol (251906-72-6) → 4a-[(4-benzoylphenyl)acetoxy]-6α,7β-diacetoxy-23-[tris(1-methylethyl)]silyloxy-5α-24-norcholane (251906-74-8)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 25 ℃; for 1h;

DOI:10.1016/S0040-4020(00)01086-3

Reference yield:

3β,23-diacetoxy-24-nor-5-cholene (64907-37-5) → 4a-[(4-benzoylphenyl)acetoxy]-6α,7β-diacetoxy-23-[tris(1-methylethyl)]silyloxy-5α-24-norcholane (251906-74-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 65 percent / RuCl₃; t-BuOOH

2: 98 percent / NaBH₄; CeCl₃

3: 97 percent / pyridine

4: 50 percent / BH₃*THF; NaOH; H₂O₂

5: 97 percent / TMSOTf

6: 95 percent / NaOH / tetrahydrofuran; ethanol

7: 76 percent / imidazole

8: 74 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; ruthenium trichloride; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; borane-THF; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; 8: Mitsunobu reaction;

DOI:10.1021/ol991057x

Reference yield:

6β-methoxy-3α,5-cyclo-5α-24-norcholan-23-ol (64907-36-4) → 4a-[(4-benzoylphenyl)acetoxy]-6α,7β-diacetoxy-23-[tris(1-methylethyl)]silyloxy-5α-24-norcholane (251906-74-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 97 percent / pyridine

2: 97 percent / Heating

3: 65 percent / RuCl₃; t-BuOOH

4: 98 percent / NaBH₄; CeCl₃

5: 97 percent / pyridine

6: 50 percent / BH₃*THF; NaOH; H₂O₂

7: 97 percent / TMSOTf

8: 95 percent / NaOH / tetrahydrofuran; ethanol

9: 76 percent / imidazole

10: 74 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; ruthenium trichloride; sodium hydroxide; sodium tetrahydroborate; cerium(III) chloride; borane-THF; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; 10: Mitsunobu reaction;

DOI:10.1021/ol991057x

upstream raw materials:

(4-benzoylphenyl)acetic acid

6α,7β-diacetoxy-23-[tris(1-methylethyl)]silyloxy-5α-24-norcholan-3β-ol

triisopropylsilyl chloride

3β,23-diacetoxy-24-nor-5-cholene