Acetic acid (S)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-5-oxo-cyclohex-1-enylmethyl ester

Base Information

• Chemical Name: Acetic acid (S)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-5-oxo-cyclohex-1-enylmethyl ester
• CAS No.: 144066-89-7
• Molecular Formula: C₁₈H₃₂O₄Si
• Molecular Weight: 340.535
• Mol file: 144066-89-7.mol

Synonyms:Acetic acid (S)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-5-oxo-cyclohex-1-enylmethyl ester

Chemical Property of Acetic acid (S)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-5-oxo-cyclohex-1-enylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (S)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-5-oxo-cyclohex-1-enylmethyl ester

There total 8 articles about Acetic acid (S)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-5-oxo-cyclohex-1-enylmethyl ester 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: 98.0%

t-butyldimethylsiyl triflate (69739-34-0) + Acetic acid (S)-3-hydroxy-2,6,6-trimethyl-5-oxo-cyclohex-1-enylmethyl ester (144066-88-6) → Acetic acid (S)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-5-oxo-cyclohex-1-enylmethyl ester (144066-89-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1039/c39920001117

Reference yield:

3-Hydroxymethyl-2,2,4-trimethyl-cyclohex-3-enone (152328-14-8) → Acetic acid (S)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-5-oxo-cyclohex-1-enylmethyl ester (144066-89-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / DMAP / CH₂Cl₂ / 1 h / 25 °C

2: 92 percent / CSA / benzene / 1 h / 70 °C

3: 1.) SeO₂, 2.) PCC, 4A molecular sieves / 1.) dioxane, 100 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C

4: 95 percent / Corey's (R)-oxazaborolidine, catecholborane / toluene / 3 h / -78 - 0 °C

5: 65 percent / TsOH / acetone; H₂O / 12 h / 25 °C

6: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

With 2,6-dimethylpyridine; dmap; selenium(IV) oxide; 4 A molecular sieve; camphor-10-sulfonic acid; toluene-4-sulfonic acid; pyridinium chlorochromate; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In dichloromethane; water; acetone; toluene; benzene;

DOI:10.1039/c39920001117

Reference yield:

Acetic acid 2,6,6-trimethyl-5-oxo-cyclohex-1-enylmethyl ester (144066-84-2) → Acetic acid (S)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-5-oxo-cyclohex-1-enylmethyl ester (144066-89-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / CSA / benzene / 1 h / 70 °C

2: 1.) SeO₂, 2.) PCC, 4A molecular sieves / 1.) dioxane, 100 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C

3: 95 percent / Corey's (R)-oxazaborolidine, catecholborane / toluene / 3 h / -78 - 0 °C

4: 65 percent / TsOH / acetone; H₂O / 12 h / 25 °C

5: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

With 2,6-dimethylpyridine; selenium(IV) oxide; 4 A molecular sieve; camphor-10-sulfonic acid; toluene-4-sulfonic acid; pyridinium chlorochromate; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In dichloromethane; water; acetone; toluene; benzene;

DOI:10.1039/c39920001117

upstream raw materials:

t-butyldimethylsiyl triflate

Acetic acid (S)-3-hydroxy-2,6,6-trimethyl-5-oxo-cyclohex-1-enylmethyl ester

3-Hydroxymethyl-2,2,4-trimethyl-cyclohex-3-enone

Acetic acid 2,6,6-trimethyl-5-oxo-cyclohex-1-enylmethyl ester