Synthesis of “9-deazaadenosine”; A new cytotoxic C-nucleoside isostere of adenosine

Synthesis of a 3′‐Deoxy‐C‐Nucleoside Phosphonate Bearing 9‐Deazaadenine as Base Moiety

“…Later, a base‐promoted epimerization occurring upon protecting group removal permitted the generation of the target compound with the desired configuration . Therefore, compound 3 , which was obtained from d ‐ribose according to a reported procedure in 9 steps, served as a convenient starting point for the synthesis of target C ‐nucleoside phosphonate 1b . First, all protons on the base moiety were masked as benzoyl groups using BzCl in pyridine as solvent, as shown in Scheme .…”

Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides

“…5 ). Like other nucleoside coupling approaches (other than the well-known Vorbrüggen coupling reaction [ 66 ], the synthesis of C-nucleosides typically gives a mixture of stereoisomers (α and β) at the anomeric carbon [ 48 – 49 54 , 62 , 67 – 68 ]. Since the naturally occurring nucleosides (and most biologically active nucleosides) are β-anomers, achieving 100% stereospecificity in C–C bond formation is an important goal, but often difficult to attain [ 62 ].…”

The transition to magic bullets – transition state analogue drug design

“…Following initial attempts to synthesise the target TS analogue of nucleoside hydrolases, the "sketch" of which bore similarities to the PNP TS blueprint, in his own laboratories Schramm approached Richard Furneaux's carbohydrate chemistry group in New Zealand where he and Peter Tyler had extensive experience synthesising iminosugars and in particular derivatives of castanospermine [72][73][74][75][76] and deoxymannojirimycin. 77 Tyler adapted the C-nucleoside synthesis of the deazapurines: deazainosine, 78 deazaadenosine, 79 and deazaguanosine (Fig. 6).…”