Complete assignment of the ¹H and ¹³C NMR spectra of cis and trans isonucleoside derivatives of purine with a tetrahydropyran ring

Abstract

(1)H and (13)C NMR chemical shifts of cis and trans isonucleoside analogues of purine in which the furanose moiety is substituted by a tetrahydropyran ring were completely assigned using one- and two-dimensional NMR experiments that include NOE, DEPT, COSY and HSQC. The significant (1)H and (13)C NMR signals differentiating between the cis and trans stereoisomers were compared.

Stereocontrolled Synthesis and Biological Evaluation of Novel Carbocyclic Nucleosides Analogues of Neplanocin F and Abacavir

“…NOESY experiments were used to determine the stereochemical configuration, and HMBC sequences ascertained the quaternary carbon chemical shifts on the purine base which were in good agreement with the N 9 -regioisomer (Figure 3). 21 The N 9 -regioisomer (±)-18 [UV (CH 2 Cl 2 ) l max = 267 nm] was also confirmed on the basis of the UV literature data. 22…”