cyanothymidine synthesis

6synthesis methods

Product Name:cyanothymidine
CAS Number:116195-58-5
Molecular formula:C11H13N3O4
Molecular Weight:251.24

Uridine, 3'-deoxy-2',5'-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-5-methyl-3'-oxo-

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Yield:-

Steps:

Multi-step reaction with 9 steps
1: sodium bicarbonate / H₂O; diethyl ether / 16 h / 15 °C
2: 4-dimethylaminopyridone / acetonitrile / 2 h / Ambient temperature
3: α,α'-azobisisobutyronitrile, tributyltin hydride / toluene / 4 h / 70 °C
4: 61 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 1 h / Ambient temperature
5: 93 percent / pyridine / 24 h / 18 °C
6: pyridine / CH₂Cl₂ / 2 h / Ambient temperature
7: 60 percent / tributyltin hydride, α,α'-azobisisobutironitrile / toluene / 3 h / 70 °C
8: 1N NaOH / methanol / 5 h / Heating; pH = 9
9: 91 percent / 0.1N NaOH / methanol / 0.5 h / Ambient temperature

References:

Calvo-Mateo;Camarasa;Diaz-Ortiz;De Las Heras;Alemany [Tetrahedron,1988,vol. 44,# 15,p. 4895 - 4903]

Thymidine, 3'-cyano-3'-deoxy-5'-O-(triphenylmethyl)- (9CI)

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References

Thymidine,3'-cyano-3'-deoxy-5'-O-[(1,1-dimethylethyl)dimethylsilyl]- (9CI)

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References

2,4(1H,3H)-Pyrimidinedione,1-(3-cyano-3-deoxy-b-D-xylofuranosyl)-5-methyl-

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References

1463-10-1 Synthesis

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References