9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]adenine

Base Information

• Chemical Name: 9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]adenine
• CAS No.: 247587-59-3
• Molecular Formula: C₂₄H₄₃N₅O₂Si₂
• Molecular Weight: 489.809
• Mol file: 247587-59-3.mol

Synonyms:9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]adenine

Chemical Property of 9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]adenine

There total 10 articles about 9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]adenine 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: 66.0%

adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) + (1R,4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-ol (247587-58-2) → 9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]adenine (247587-59-3) + 7-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]adenine

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; at 20 ℃;

DOI:10.1080/15257779908041505

Reference yield:

adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) + (1R,4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-ol (247587-58-2) → 9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]adenine (247587-59-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; at 20 ℃;

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]adenine (247587-59-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / imidazole / dimethylformamide / 20 °C

2: 92 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

3: 97 percent / HCOONH₄ / Pd/C / 14 h / Heating

4: MnO₂ / CH₂Cl₂ / 21 h / 20 °C

5: 91 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 1 h

6: 66 percent / PPh₃; DEAD / dioxane / 20 °C

With 1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; cerium(III) chloride; ammonium formate; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Substitution / 3: Hydrogenolysis / 4: Oxidation / 5: Reduction / 6: Substitution;

DOI:10.1021/jo9908288

upstream raw materials:

adenine

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

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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

9-[(1R,4S,5R)-3-hydroxy-4-hydroxymethylcyclohexanyl]adenine