79378-86-2

Upstream product

• 79378-83-9 4-Amino-6-phenyl-8-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-7(8H)-pteridinon 
• 101-97-3 Ethyl 2-phenylethanoate 
• 79378-81-7 4-amino-6-phenyl-7(8H)-pteridinone 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 

Relevant academic research and scientific papers

Nucleosides part LXVI I[1]: Synthesis of 4-amino-7(8H) pteridinone-N8-nucleosides-structural analogs of adenosine

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.

Nucleosides, XXXVI. - Synthesis and Properties of 4-Amino-8-β-D-ribofuranosyl-7(8H)-pteridinone and its 2- and 6-Phenyl Derivatives.

4-Amino-7(8H)-pteridinone (5) and its 2- and 5-phenyl derivatives (6-8) are converted by the Silyl-Hilbert-Johnson method to the corresponding acylated N-8-ribosides (15-18, 23, 24).Deacylation led to the free pteridine nucleosides (19-22, 25) which can b