(S)-1-Allyl-5-(2-hydroxy-2-methyl-pent-4-enyl)-2,6,6-trimethyl-5-trimethylsilanyloxy-cyclohex-2-enol

Base Information

• Chemical Name: (S)-1-Allyl-5-(2-hydroxy-2-methyl-pent-4-enyl)-2,6,6-trimethyl-5-trimethylsilanyloxy-cyclohex-2-enol
• CAS No.: 244623-34-5
• Molecular Formula: C₂₁H₃₈O₃Si
• Molecular Weight: 366.616
• Mol file: 244623-34-5.mol

Synonyms:(S)-1-Allyl-5-(2-hydroxy-2-methyl-pent-4-enyl)-2,6,6-trimethyl-5-trimethylsilanyloxy-cyclohex-2-enol

Chemical Property of (S)-1-Allyl-5-(2-hydroxy-2-methyl-pent-4-enyl)-2,6,6-trimethyl-5-trimethylsilanyloxy-cyclohex-2-enol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-Allyl-5-(2-hydroxy-2-methyl-pent-4-enyl)-2,6,6-trimethyl-5-trimethylsilanyloxy-cyclohex-2-enol

There total 9 articles about (S)-1-Allyl-5-(2-hydroxy-2-methyl-pent-4-enyl)-2,6,6-trimethyl-5-trimethylsilanyloxy-cyclohex-2-enol 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: 65.0%

(S)-2,6,6-Trimethyl-5-(2-oxo-propyl)-5-trimethylsilanyloxy-cyclohex-2-enone (244623-33-4) + allylmagnesium bromide (1730-25-2) → (S)-1-Allyl-5-(2-hydroxy-2-methyl-pent-4-enyl)-2,6,6-trimethyl-5-trimethylsilanyloxy-cyclohex-2-enol (244623-34-5)

Guidance literature:

In diethyl ether; at 0 ℃;

DOI:10.1016/S0040-4039(99)00902-8

Reference yield:

(1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one (36616-60-1) → (S)-1-Allyl-5-(2-hydroxy-2-methyl-pent-4-enyl)-2,6,6-trimethyl-5-trimethylsilanyloxy-cyclohex-2-enol (244623-34-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 60 percent / Li; liq.NH₃

2: 35 percent / tetrahydrofuran / ultrasonic irr.

3: 90 percent / Zn / tetrahydrofuran / sonication

4: 88 percent / TPAP; NMMO; 4 Angstroem mol. sieves / CH₂Cl₂

5: 95 percent / TBAF / dimethylformamide / 1.5 h

6: 95 percent / KH / tetrahydrofuran / 12 h / -10 °C

7: 60 percent / PdCl₂; CuCl; O₂ / dimethylformamide; H₂O / 48 h

8: 60 percent / O₃; Cu(AcO)2; FeSO₄ / CH₂Cl₂; methanol / -78 °C

9: 65 percent / diethyl ether / 0 °C

With tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; oxygen; copper diacetate; lithium; potassium hydride; ozone; iron(II) sulfate; 4-methylmorpholine N-oxide; copper(l) chloride; palladium dichloride; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 1: Alkylation / 2: Addition / 3: Addition / 4: Oxidation / 5: Alkylation / 6: Alkylation / 7: Oxidation / 8: ozonolyzis, Criege rearrangement / 9: Addition;

DOI:10.1016/S0040-4039(99)00902-8

Reference yield:

(R)-Carvone (6485-40-1,2244-16-8) → (S)-1-Allyl-5-(2-hydroxy-2-methyl-pent-4-enyl)-2,6,6-trimethyl-5-trimethylsilanyloxy-cyclohex-2-enol (244623-34-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 98 percent / H₂O₂; NaOH / 0 °C

2: 60 percent / Li; liq.NH₃

3: 35 percent / tetrahydrofuran / ultrasonic irr.

4: 90 percent / Zn / tetrahydrofuran / sonication

5: 88 percent / TPAP; NMMO; 4 Angstroem mol. sieves / CH₂Cl₂

6: 95 percent / TBAF / dimethylformamide / 1.5 h

7: 95 percent / KH / tetrahydrofuran / 12 h / -10 °C

8: 60 percent / PdCl₂; CuCl; O₂ / dimethylformamide; H₂O / 48 h

9: 60 percent / O₃; Cu(AcO)2; FeSO₄ / CH₂Cl₂; methanol / -78 °C

10: 65 percent / diethyl ether / 0 °C

With sodium hydroxide; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; oxygen; copper diacetate; lithium; potassium hydride; ozone; iron(II) sulfate; 4-methylmorpholine N-oxide; copper(l) chloride; palladium dichloride; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 1: Epoxidation / 2: Alkylation / 3: Addition / 4: Addition / 5: Oxidation / 6: Alkylation / 7: Alkylation / 8: Oxidation / 9: ozonolyzis, Criege rearrangement / 10: Addition;

DOI:10.1016/S0040-4039(99)00902-8

upstream raw materials:

(S)-2,6,6-Trimethyl-5-(2-oxo-propyl)-5-trimethylsilanyloxy-cyclohex-2-enone

allylmagnesium bromide

(1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one

(R)-Carvone