185329-67-3Relevant academic research and scientific papers
Nucleosides part LXVI I[1]: Synthesis of 4-amino-7(8H) pteridinone-N8-nucleosides-structural analogs of adenosine
Jungmann, Oliver,Pfleiderer, Wolfgang
experimental part, p. 550 - 585 (2010/07/14)
Various 4-amino-7(8H)pteridones (6, 12, 14, 15, 20, 22) have been glycosylated with 1-chloro-2'-deoxy-D-ribofuranose derivatives (25, 26) applying the new DBU-salt method to form the N8-2'-deoxy-D-ribofuranosides (27-36) which can be regarded as 2'-deoxyadenosine analogs. Analogously reacted the 2-N,N-dimethyl-amino-methyleneimino-7(8H)pteridones (43-48) to give preferentially the corresponding N8-ss-D-anomers (49-55). Ribosylation with 1-bromo-2,3,5-tri-O-benzoyl-a-D-ribofuranose (56) proceeded as well with 6, 12, 15, 45, and 46 to yield to N8-ss-D-ribofuranosides 57-61. Sugar deprotection led to the free N8-2'-deoxy-ss-D-ribofuranosides 37-42 and N8-ss-D-ribofurano-sides 62-65, respectively. Glycosylations via the silyl-method under Vorbruggen conditions led with 6, 12 and 15 to the same results, however, 4-amino-6-phenyl-7(8H)pteridone (14) reacted differently forming the N1-ss-D-ribofuranosides (71, 79) and the N1-2'-deoxy - and ss-D-ribofuranosides 73, 74, 77, 78. The assignments of the structures have been achieved by 1H-NMR- and UV-spectra. C,H,N-elemental analyses account for the composition.
A new efficient method in nucleoside synthesis
Jungmann, Oliver,Pfleiderer, Wolfgang
, p. 8355 - 8358 (2007/10/03)
A new stereo- and regioselective synthesis for adenosine analogous nucleosides is described. Starting from 2- and 6-substituted 4-amino-7(8H)-pteridinones, DBU deprotonation and the ribosylation with an α-haloribofuranose derivative leads to the corresponding pteridine-N-8-β-D-nucleosides in reasonably good yields.
