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

Base Information

Chemical Name:3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propan-1-ol
CAS No.:408357-91-5
Molecular Formula:C₁₈H₃₆O₂Si
Molecular Weight:312.568
Hs Code.:

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

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

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

There total 13 articles about 3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propan-1-ol 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:

: 130583-95-8
(4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-2,2,6-trimethylcyclohexan-1-one

: 408357-91-5
3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propan-1-ol

Guidance literature:: Multi-step reaction with 8 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

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:

: 3-[4-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-propionaldehyde

: 408357-91-5
3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propan-1-ol

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h;

Reference yield:

: 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
(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one

: 408357-91-5
3-[(4R)-4-tert-butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl]propan-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: Et₃N, DMAP

3: KOH, H₂O

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

5: NABH₄

6: pyridine

With pyridine; dmap; potassium hydroxide; sodium tetrahydroborate; water; triethylamine; benzoic acid; tris-(triphenylsiloxy)-vanadium oxide; In xylene;
DOI:10.1039/a901116a