(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1,4-cyclohexanedione

Base Information

• Chemical Name: (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1,4-cyclohexanedione
• CAS No.: 376353-72-9
• Molecular Formula: C₁₈H₃₆O₄Si₂
• Molecular Weight: 372.652
• Mol file: 376353-72-9.mol

Synonyms:(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1,4-cyclohexanedione

Chemical Property of (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1,4-cyclohexanedione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1,4-cyclohexanedione

There total 1 articles about (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1,4-cyclohexanedione 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%

(3R,5R)-3,5-bis[tert-butyl(dimethyl)silyloxy]-4-hydroxycyclohexanone (141404-08-2) → (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1,4-cyclohexanedione (376353-72-9)

Guidance literature:

With sodium periodate; ruthenium trichloride; In tetrachloromethane; acetonitrile; at 20 ℃; for 22h;

DOI:10.1021/jm020007m

Reference yield: 64.0%

methyl (trimethylsilyl)acetate (2916-76-9) + (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1,4-cyclohexanedione (376353-72-9) → [(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-oxo-cyclohexylidene]acetic acid methyl ester (376353-73-0)

Guidance literature:

methyl (trimethylsilyl)acetate; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h; Peterson olefination;

(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1,4-cyclohexanedione; In tetrahydrofuran; hexane; at -78 ℃; for 0.2h; Further stages.;

DOI:10.1021/jm020007m

Reference yield:

(3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1,4-cyclohexanedione (376353-72-9) → (20R)-1α,25-dihydroxy-2β-ethyl-19-norvitamin D3

Guidance literature:

Multi-step reaction with 9 steps

1.1: LDA / tetrahydrofuran; hexane / 0.25 h / -78 °C / Peterson olefination

1.2: 64 percent / tetrahydrofuran; hexane / 0.2 h / -78 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / 0 - 20 °C

2.2: hexane; tetrahydrofuran / 3.67 h / -78 °C

3.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / 0 - 20 °C

3.2: hexane; tetrahydrofuran / 3.67 h / -78 °C

3.3: DIBALH / toluene; CH₂Cl₂ / 1 h / -78 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 0 °C

5.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

6.1: 60 percent / H₂O₂ / CH₂Cl₂; H₂O / 1 h / 0 °C

7.1: phenyllithium / tetrahydrofuran; cyclohexane; diethyl ether / 0.33 h / -78 °C

7.2: 9 percent / tetrahydrofuran; cyclohexane; diethyl ether / 22 h / -78 - 0 °C

8.1: 64 percent / tetrabutylammonium fluoride / tetrahydrofuran / 23 h / 20 °C

9.1: 11 percent / H₂ / tris(triphenylphosphine)rhodium(I) chloride / benzene / 9.5 h / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; phenyllithium; lithium diisopropyl amide; Wilkinson's catalyst; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; water; benzene; 2.2: Wittig reaction / 3.2: Wittig reaction / 7.2: Wittig-Horner coupling;

DOI:10.1021/jm020007m

upstream raw materials:

(3R,5R)-3,5-bis[tert-butyl(dimethyl)silyloxy]-4-hydroxycyclohexanone

Downstream raw materials:

[(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-oxo-cyclohexylidene]acetic acid methyl ester

[(3'R,5'R)-3',5'-bis[(tert-butyldimethylsilyl)oxy]-4'-ethylidenecyclohexylidene]acetic acid methyl ester