4-Cyclohexene-1,3-diol, 1-[(benzoyloxy)methyl]-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-4, 6,6-trimethyl-, (1S,3S)-

Base Information

• Chemical Name: 4-Cyclohexene-1,3-diol, 1-[(benzoyloxy)methyl]-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-4, 6,6-trimethyl-, (1S,3S)-
• CAS No.: 595568-53-9
• Molecular Formula: C24H38O5Si
• Molecular Weight: 434.648
• Mol file: 595568-53-9.mol

Synonyms:

Chemical Property of 4-Cyclohexene-1,3-diol, 1-[(benzoyloxy)methyl]-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-4, 6,6-trimethyl-, (1S,3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Cyclohexene-1,3-diol, 1-[(benzoyloxy)methyl]-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-4, 6,6-trimethyl-, (1S,3S)-

There total 17 articles about 4-Cyclohexene-1,3-diol, 1-[(benzoyloxy)methyl]-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-4, 6,6-trimethyl-, (1S,3S)- 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: 62.0%

(5S)-3-(tert-butyldimethylsiloxymethyl)-5-hydroxy-5-benzoyloxymethyl-2,4,4-trimethyl-cyclohex-2-en-1-one (595568-60-8) → (4S,5R)-2-(tert-butyldimethylsiloxymethyl)-4,6-dihydroxy-4-benzoyloxymethyl-1,3,3-trimethyl-cyclohex-1-ene (595568-53-9)

Guidance literature:

With sodium tris(acetoxy)borohydride; In acetic acid; acetonitrile; at 0 - 20 ℃; for 22h;

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

Reference yield:

2,2-dimethyl-1,3-cyclohexanedione (562-13-0) → (4S,5R)-2-(tert-butyldimethylsiloxymethyl)-4,6-dihydroxy-4-benzoyloxymethyl-1,3,3-trimethyl-cyclohex-1-ene (595568-53-9)

Guidance literature:

Multi-step reaction with 17 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

13.1: 98 percent / pyridine / toluene; CH₂Cl₂ / 2.25 h / -78 - 20 °C

14.1: 44 percent / selenium dioxide / dioxane / 2 h / 100 °C

15.1: 86 percent / hexane; diethyl ether; tetrahydrofuran / 1.33 h / -78 - 20 °C

16.1: 95 percent / pyridinium chlorochromate; sodium acetate / CH₂Cl₂ / 3 h / 0 °C

17.1: 62 percent / sodium triacetoxyborohydride / acetic acid; acetonitrile / 22 h / 0 - 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; selenium(IV) oxide; cerium(III) chloride; diethyl (2R,3R)-tartrate; 2,6-dichloro-benzonitrile; camphor-10-sulfonic acid; iodine; tert.-butyl lithium; sodium acetate; sodium tris(acetoxy)borohydride; hydrazine hydrate; triethylamine; pyridinium chlorochromate; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; decane; ethanol; hexane; dichloromethane; water; acetic acid; toluene; acetonitrile; 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:

tert-butyldimethylsilyl chloride (18162-48-6) → (4S,5R)-2-(tert-butyldimethylsiloxymethyl)-4,6-dihydroxy-4-benzoyloxymethyl-1,3,3-trimethyl-cyclohex-1-ene (595568-53-9)

Guidance literature:

Multi-step reaction with 10 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

6.1: 98 percent / pyridine / toluene; CH₂Cl₂ / 2.25 h / -78 - 20 °C

7.1: 44 percent / selenium dioxide / dioxane / 2 h / 100 °C

8.1: 86 percent / hexane; diethyl ether; tetrahydrofuran / 1.33 h / -78 - 20 °C

9.1: 95 percent / pyridinium chlorochromate; sodium acetate / CH₂Cl₂ / 3 h / 0 °C

10.1: 62 percent / sodium triacetoxyborohydride / acetic acid; acetonitrile / 22 h / 0 - 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; selenium(IV) oxide; cerium(III) chloride; diethyl (2R,3R)-tartrate; sodium acetate; sodium tris(acetoxy)borohydride; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; decane; hexane; dichloromethane; acetic acid; toluene; acetonitrile; 4.1: Luche reduction / 5.1: Sharpless asymmetric epoxidation;

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

upstream raw materials:

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

2,2-dimethyl-1,3-cyclohexanedione

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

benzoic acid (S)-3-(tert-butyl-dimethyl-silanyloxymethyl)-1,5-bis-methoxymethoxy-2,2,4-trimethyl-cyclohex-3-enyl ester