ChemicalBook CAS DataBase List 3'-Deoxytubercidin

3'-Deoxytubercidin synthesis

8synthesis methods

Product Name:3'-Deoxytubercidin
CAS Number:40725-89-1
Molecular formula:C11H14N4O3
Molecular Weight:250.26

69-33-0 Synthesis

69-33-0
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40725-89-1
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Yield:40725-89-1 43%

Reaction Conditions:

Stage #1: tubercidinwith 2-acetoxy-2-methylpropanoyl chloride;sodium iodide in acetonitrile; for 1.5 h;
Stage #2: with palladium on activated charcoal;hydrogen in methanol;
Stage #3: with ammonia in methanol;

Steps:

General procedure 1 (conversion of ribo-nucleoside into 3'-deoxy analogue)

General procedure: Nal (10 eq.) was dissolved in anhydrous MeCN (10mL/mmol SM), and stirred for 5min under argon. Next, a-acetoxyisobutyrylchloride (3.5 eq.) was added, giving a white precipitate. The mixture was stirred vigorously for another 5 - 10min, after which the appropriate ribonucleoside (1 eq.) was added in one portion. The resulting mixture was stirred for 1 .5H after which TLC showed full conversion of SM. The mixture was poured in aq. sat. NaHC0₃ / aq. sat. Na₂S₂0₃ solution. Next, CHCI₃ was added, and the layers separated. The water layer was extracted with CHCI₃ twice more. Organic layers were combined, dried over Na₂S0₄, filtered and evaporated. The resulting oil was dissolved in EtOH (7.5 mL / mmol SM) and 1 M aq. NaOAc solution (2.5 mL / mmol SM) was added. Next, the flask was purged with N₂, after which a cat. amount of Pd/C was added. Next, the N₂- atmosphere was exchanged for H₂ (balloon; no bubbling) and the mixture stirred overnight. Next, the mixture was purged with N₂ to remover residual H₂-gas, and filtered over a pad of Celite. The mixture was evaporated till dryness, and partitioned between EA and aq. sat. NaHC0₃ / aq. sat. Na₂S₂0₃ solution. Layers were separated and the water layer extracted twice more with EA. Organic layers were combined, dried over Na₂S0₄, filtered and evaporated. The resulting oil was dissolved in 7N NH₃ in MeOH and stirred overnight. The solvent was removed, and the residue purified by column chromatography 0→ 15 % MeOH / DCM.