(1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol

Base Information

• Chemical Name: (1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol
• CAS No.: 247587-51-5
• Molecular Formula: C₂₀H₃₂O₃Si
• Molecular Weight: 348.558
• Mol file: 247587-51-5.mol

Synonyms:(1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol

Chemical Property of (1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol

There total 1 articles about (1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol 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: 71.0%

((1R,2S,4R,6R)-4-Benzyloxy-1-methyl-7-oxa-bicyclo[4.1.0]hept-2-yloxy)-tert-butyl-dimethyl-silane → (1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol (247587-51-5)

Guidance literature:

With 2,2,6,6-tetramethylpiperidinyl-lithium; diethylaluminium chloride; In toluene; benzene; at 0 ℃; for 30h;

DOI:10.1021/jo9908288

Reference yield: 74.0%

(1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol (247587-51-5) → (1R,2S,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol (247587-52-6) + (1R,2R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol

Guidance literature:

(1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 0 - 20 ℃;

With sodium hydroxide; dihydrogen peroxide; In ethanol; at 20 ℃; for 24h;

DOI:10.1021/jo9908288

Reference yield:

(1R,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclohexanol (247587-51-5) → 9-[(1S,4R,5S)-5-hydroxy-4-hydroxymethyl-2-cyclohexenyl]adenine (247587-60-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

1.2: 74 percent / 35 percent H₂O₂; 2N NaOH / ethanol / 24 h / 20 °C

2.1: 70 percent / imidazole / dimethylformamide / 20 °C

3.1: 92 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4.1: 97 percent / HCOONH₄ / Pd/C / 14 h / Heating

5.1: MnO₂ / CH₂Cl₂ / 21 h / 20 °C

6.1: 91 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1 h

7.1: 66 percent / PPh₃; DEAD / dioxane / 20 °C

8.1: TFA / H₂O / 20 °C

With 1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; cerium(III) chloride; ammonium formate; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: hydroboration / 1.2: Oxidation / 2.1: Substitution / 3.1: Substitution / 4.1: Hydrogenolysis / 5.1: Oxidation / 6.1: Reduction / 7.1: Substitution / 8.1: Substitution;

DOI:10.1021/jo9908288

Downstream raw materials:

(1R,2S,3S,5R)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-hydroxymethyl-cyclohexanol

9-[(1S,4R,5S)-5-hydroxy-4-hydroxymethyl-2-cyclohexenyl]adenine

(4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-one

(1R,4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-ol