9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]-2-amino-6-chloropurine

Base Information

• Chemical Name: 9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]-2-amino-6-chloropurine
• CAS No.: 262372-06-5
• Molecular Formula: C₂₄H₄₂ClN₅O₂Si₂
• Molecular Weight: 524.254
• Mol file: 262372-06-5.mol

Synonyms:9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]-2-amino-6-chloropurine

Chemical Property of 9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]-2-amino-6-chloropurine

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]-2-amino-6-chloropurine

There total 6 articles about 9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]-2-amino-6-chloropurine 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:

C25H54O3Si3 + 2-amino-6-chloro-purine → 9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]-2-amino-6-chloropurine (262372-06-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; at 20 ℃; for 49.5h;

Reference yield:

2-Amino-6-chloropurin (10310-21-1) + (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]-2-amino-6-chloropurine (262372-06-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane;

DOI:10.1081/NCN-100002360

Reference yield:

(1R,2S,3S,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-(tert-butyldimethylsilyloxymethyl)cyclohexanol (247587-54-8) → 9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]-2-amino-6-chloropurine (262372-06-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / Et₃N / CH₂Cl₂

2: 76 percent / HCOONH₄ / Pd/C / methanol

3: 48 percent / MnO₂ / CH₂Cl₂

4: 91 percent / NaBH₄; CeCl₃*7H₂O

5: diethyl azodicarboxylate; PPh₃ / dioxane

With manganese(IV) oxide; sodium tetrahydroborate; cerium(III) chloride; ammonium formate; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1081/NCN-100002360

upstream raw materials:

2-Amino-6-chloropurin

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

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

(1R,3R,4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxy-3-methanesulfonyloxycyclohexanol

Downstream raw materials:

(1S,4R,5S)-9-(5-hydroxy-4-hydroxymethyl-2-cyclohexen-1-yl)guanine