2-(Phenylthio)ethyl as a novel two-stage base protecting group for thymidine analogues

Synlett

Volumn , Issue 6, 2006, Pages 845-848

  D'Onofrio, Jennifer ^a   De Napoli, Lorenzo ^a   Di Fabio, Giovanni ^a   Montesarchio, Daniela ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Mitsunobu reactions; Oligonucleotides; Protecting groups; Solid phase synthesis; Thymidine

Indexed keywords

ALCOHOL DERIVATIVE; OLIGONUCLEOTIDE; PROTECTIVE AGENT; PYRIMIDINE; RIBOSE; SULFIDE; SULFONE; THYMIDINE DERIVATIVE; THYMINE;

ALKALINITY; ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; ELIMINATION REACTION; MITSUNOBU REACTION; OXIDATION; PROTECTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 33645789610     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-933147     Document Type: Article

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18. +].
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23. +].
24. 3-pyridine (1:0.05)], affording 980 mg (1.23 mmol, 90%) of pure 3.
25. +].
26. 3 at 55 °C after an overnight treatment was only partial, requiring longer reaction times to go to completion (ca. 72 h). On the other hand, a 0.1 M NaOH solution ensured complete thymine deprotection after an overnight treatment at 50 °C, i.e. conditions usually adopted also for oligonucleotide deprotection and detachment from the solid support.
27. -.