3-Cyclohexene-1-methanol, 3-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-hydroxy-2,2,4-trimethyl- , (1S)-

Base Information

• Chemical Name: 3-Cyclohexene-1-methanol, 3-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-hydroxy-2,2,4-trimethyl- , (1S)-
• CAS No.: 595568-56-2
• Molecular Formula: C17H34O3Si
• Molecular Weight: 314.541
• Mol file: 595568-56-2.mol

Synonyms:

Chemical Property of 3-Cyclohexene-1-methanol, 3-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-hydroxy-2,2,4-trimethyl- , (1S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Cyclohexene-1-methanol, 3-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-hydroxy-2,2,4-trimethyl- , (1S)-

There total 12 articles about 3-Cyclohexene-1-methanol, 3-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-hydroxy-2,2,4-trimethyl- , (1S)- 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:

2,2-dimethyl-1,3-cyclohexanedione (562-13-0) → (4S)-2-(tert-butyldimethylsiloxymethyl)-4-hydroxy-4-(hydroxymethyl)-1,3,3-trimethyl-cyclohex-1-ene (595568-56-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 88 percent / (+/-)-camphor-10-sulfonic acid / benzene / 0.5 h / Heating

2.1: LiHMDS / hexane; tetrahydrofuran / 1 h / -78 °C

2.2: 89 percent / hexane; tetrahydrofuran / 3.5 h / -78 - 20 °C

3.1: hydrazine hydrate; triethylamine / ethanol / 312 h / Heating

4.1: 9.2 g / DBN; I₂ / diethyl ether / 0.5 h / 20 °C

5.1: t-BuLi / pentane; tetrahydrofuran / 0.5 h / -78 °C

5.2: pentane; tetrahydrofuran / 1.67 h / -78 - 20 °C

6.1: CeCl₃*7H₂O; NaBH₄ / methanol / 0.5 h / 0 °C

7.1: 2.75 g / HCl / H₂O / 0.5 h / 20 °C

8.1: 92 percent / imidazole / CH₂Cl₂ / 14 h / 20 °C

9.1: 87 percent / CH₂Cl₂ / 16 h / 26 °C

10.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

10.2: hexane; tetrahydrofuran / 1.67 h / -78 - 20 °C

11.1: 718 mg / CeCl₃*7H₂O; NaBH₄ / methanol / 0.5 h / 0 °C

12.1: tert-butylhydroperoxide; (+)-L-diethyl tartrate; titanium tetraisopropoxide / CH₂Cl₂; decane / 24 h / -23 °C

12.2: 260 mg / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; diethyl (2R,3R)-tartrate; 2,6-dichloro-benzonitrile; camphor-10-sulfonic acid; iodine; tert.-butyl lithium; hydrazine hydrate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; decane; ethanol; hexane; dichloromethane; water; pentane; benzene; 6.1: Luche reduction / 11.1: Luche reduction / 12.1: Sharpless asymmetric epoxidation;

DOI:10.1016/S0040-4020(03)00699-9

Reference yield:

2-(tert-butyldimethylsiloxymethyl)-4-hydroxymethyl-1,3,3-trimethyl-cyclohexa-1,4-diene (595568-54-0) → (4S)-2-(tert-butyldimethylsiloxymethyl)-4-hydroxy-4-(hydroxymethyl)-1,3,3-trimethyl-cyclohex-1-ene (595568-56-2)

Guidance literature:

2-(tert-butyldimethylsiloxymethyl)-4-hydroxymethyl-1,3,3-trimethyl-cyclohexa-1,4-diene; With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; In decane; dichloromethane; at -23 ℃; for 24h;

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(03)00699-9

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (4S)-2-(tert-butyldimethylsiloxymethyl)-4-hydroxy-4-(hydroxymethyl)-1,3,3-trimethyl-cyclohex-1-ene (595568-56-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 92 percent / imidazole / CH₂Cl₂ / 14 h / 20 °C

2.1: 87 percent / CH₂Cl₂ / 16 h / 26 °C

3.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

3.2: hexane; tetrahydrofuran / 1.67 h / -78 - 20 °C

4.1: 718 mg / CeCl₃*7H₂O; NaBH₄ / methanol / 0.5 h / 0 °C

5.1: tert-butylhydroperoxide; (+)-L-diethyl tartrate; titanium tetraisopropoxide / CH₂Cl₂; decane / 24 h / -23 °C

5.2: 260 mg / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; diethyl (2R,3R)-tartrate; In tetrahydrofuran; methanol; decane; hexane; dichloromethane; 4.1: Luche reduction / 5.1: Sharpless asymmetric epoxidation;

DOI:10.1016/S0040-4020(03)00699-9

upstream raw materials:

2-(tert-butyldimethylsiloxymethyl)-4-hydroxymethyl-1,3,3-trimethyl-cyclohexa-1,4-diene

2,2-dimethyl-1,3-cyclohexanedione

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

(5S)-3-(tert-butyldimethylsiloxymethyl)-5-hydroxy-5-benzoyloxymethyl-2,4,4-trimethyl-cyclohex-2-en-1-one

(4S)-2-(tert-butyldimethylsiloxymethyl)-4,6-dihydroxy-4-benzoyloxymethyl-1,3,3-trimethyl-cyclohex-1-ene

(4S,5R)-2-(tert-butyldimethylsiloxymethyl)-4,6-dihydroxy-4-benzoyloxymethyl-1,3,3-trimethyl-cyclohex-1-ene