72277-35-1Relevant articles and documents
Diastereoselective synthesis of 1,2-O-isopropylidene-1,6-dioxaspiro[4,4]nonane applying the methodology of generation of radical cations under non-oxidizing conditions
Sartillo-Piscil, Fernando,Vargas, Mónica,Anaya De Parrodi, Cecilia,Quintero, Leticia
, p. 3919 - 3921 (2003)
We report the stereoselective synthesis of an optically pure spiroketal via an intramolecular tandem hydrogen abstraction reaction promoted by an alkoxy radical. Expanding the use of alkene radical cation under non-oxidizing conditions in the synthetic sc
114. Aza-claisen rearrangement: Synthesis of 5'-branched 5'- aminothymidines
Ammenn, Jochen,Altmann, Karl-Heinz,Bellus, Daniel
, p. 1589 - 1606 (2007/10/03)
The syntheses of both diastereoisomers of 5'-ethyl-substituted thymidine dimers, the (5'R)- and (5'S)-configurated 33a and 33b, respectively, in which the natural phosphodiester linkage is replaced by an amide group (C(3')- CH2CONH-CH(5')(Et)), are described. Their fully protected derivatives 35a and 35b, respectively, are suitable for incorporation into antisense oligonucleotides. Unexpectedly, an attempted Pd(II)-catalysed aza-Claisen rearrangement of trichloroacetimidate 7 provided the diastereoisomerically pure cyclopropane derivative 17, whose structure was confirmed by X-ray analysis.