First synthesis of 2'-deoxyfluoropuromycin analogues: experimental insight into the mechanism of the Staudinger reaction.

@article{Charafeddine2007FirstSO,
  title={First synthesis of 2'-deoxyfluoropuromycin analogues: experimental insight into the mechanism of the Staudinger reaction.},
  author={Adib Charafeddine and W. Dayoub and Hubert Chapuis and P. Strazewski},
  journal={Chemistry},
  year={2007},
  volume={13 19},
  pages={
          5566-84
        }
}
The N(6),N(6)-dedimethyl-2'-deoxyfluoro analogue of puromycin (= 3'-deoxy-N(6),N(6)-dimethyl-3'-[O-methyltyrosylamido]adenosine), its 2',3'-regioisomer and a 3'-cytidyl-5'-(2'-deoxyfluoro)puromycyl dinucleotide analogue were synthesized following an approach involving i) the diastereospecific nitrite-assisted formation of a lyxo nucleosidic 2',3'-epoxide from an adenosine-2',3'-ditriflate derivative in a biphasic solvent mixture; ii) the regio- and stereoselective epoxide ring opening with… Expand
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UNEXPECTED REACTIONS OF (1R)2,3,4,6-TETRA-O-ACETYL-1-AZIDO-D-GALACTOPYRANOSYL CYANIDE AND THE DERIVED CARBOXAMIDE WITH TRIPHENYLPHOSPHINE
Abstract Staudinger reaction of acetylated (1 R )-1-azido-D-galactopyranosyl cyanide ( 1 ) with triphenylphosphine in diethyl ether led to the isolation of a crystalline phosphazide ( 2 ),Expand
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