Synthesis of 3',3'-difluoro-2'- hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides.

Nucleosides with a carbon bridge between sugar and nucleobase: The chemistry of 1'-homonucleosides and reversed nucleosides. A review

Conformational properties and the energy barriers between the anti and the syn configurations of 3TC, ddC, AZT and d4T have been examined using the density functional theory. For 3TC, ddC and AZT the global minimum structure is the syn configuration of pyrimidine unit. Only thymine ring of d4T is at the anti conformation. Changing from the syn to the anti configuration, the furanose ring conformation is not generally affected for all compounds under consideration.

Preferred conformations of some pyrimidine nucleoside reverse transcriptase inhibitors (NRTIs)

Synthesis of carbocyclic homo-N-nucleosides from iridoids

We present a mechanistic investigation of Pd-catalyzed allylic substitution of cyclic gem-difluorinated carbonates 1 and 4, previously employed in the synthesis of 3',3'-difluoro-2'-hydroxymethyl-4',5'-unsaturated carbocyclic nucleosides in 17 steps. The substitution features a reversal of regioselectivity caused by fluorine.

https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-4-18.pdf

Understanding the mechanism of Pd-catalyzed allylic substitution of the cyclic difluorinated carbonates

A series of o ne t wo c arbonucleoside (OTC) analogues of thymine was synthetized and their conformation was studied by AM1 theoretical calculations. The low-energy conformations of Compound 1 and 2′,3′-dideoxythymidine, showed a degree of steric congruity.

1,2-Disubstituted Carbocyclic Analogues of Thymine Nucleosides

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1,2-Disubstituted Carbocyclic Analogues of Thymine Nucleosides