3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propyl acetate

Base Information

• Chemical Name: 3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propyl acetate
• CAS No.: 245504-01-2
• Molecular Formula: C₂₀H₃₈O₃Si
• Molecular Weight: 354.605
• Mol file: 245504-01-2.mol

Synonyms:3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propyl acetate

Chemical Property of 3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propyl acetate

There total 13 articles about 3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propyl acetate 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: 94.0%

acetic anhydride (108-24-7) + 3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propan-1-ol (408357-91-5) → 3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propyl acetate (245504-01-2)

Guidance literature:

With pyridine; at 20 ℃; for 16h;

Reference yield:

(4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-2,2,6-trimethylcyclohexan-1-one (130583-95-8) → 3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propyl acetate (245504-01-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

1.2: tetrahydrofuran; hexane / 0.5 h / 0 °C

2.1: 14.56 g / aq. KOH / methanol / 1 h / 20 °C

3.1: 100 percent / (Ph₃SiO)3VO; PhCO₂H / xylene / 3.5 h / Heating

4.1: 99 percent / NaBH₄ / methanol / 0.17 h / 0 °C

5.1: 91 percent / pyridine / 1 h / 20 °C

6.1: 89 percent / 18-crown-6 / dimethylsulfoxide / 16 h / 120 °C

7.1: DIBAL-H / diethyl ether; hexane / 1 h / 0 °C

8.1: 4.66 g / NaBH₄ / methanol / 0.33 h / 0 °C

9.1: 94 percent / pyridine / 16 h / 20 °C

With pyridine; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; 18-crown-6 ether; tris-(triphenylsiloxy)-vanadium oxide; diisobutylaluminium hydride; benzoic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dimethyl sulfoxide; xylene;

Reference yield:

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one (20548-02-1,55058-51-0,60686-81-9,60686-82-0,82977-53-5,90082-06-7,90129-05-8,99881-84-2,60046-50-6) → 3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propyl acetate (245504-01-2)

Guidance literature:

Multi-step reaction with 8 steps

1: Et₃N, DMAP

3: KOH, H₂O

4: PhCO₂H / (Ph₃SiO)3VO / xylene / Heating

5: NABH₄

6: pyridine

8: pyridine

With pyridine; dmap; potassium hydroxide; sodium tetrahydroborate; water; triethylamine; benzoic acid; tris-(triphenylsiloxy)-vanadium oxide; In xylene;

DOI:10.1039/a901116a

upstream raw materials:

acetic anhydride

3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propan-1-ol

(4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-2,2,6-trimethylcyclohexan-1-one

[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]acetaldehyde