32865-76-2Relevant articles and documents
2'-Deoxypuromycin: Synthesis and antiviral evaluation
Motawia,Meldal,Sofan,Stein,Pedersen,Nielsen
, p. 265 - 270 (2007/10/02)
A new synthesis of 2'-deoxypuromycin (18) as well as its α-anomer 17 is described. Reaction of 1,5-di-O-acetyl-2,3-dideoxy-3-phthalimido-β-D-erythro-pentofuranose (3) with silylated 6-dimethylaminopurine using trimethylsilyl trifluoromethanesulfonate as catalyst afforded the α and β nucleosides 7 and 12 in 15 and 25% yield, respectively. After deblocking of both amino and hydroxy groups with methylamine in ethanol, the nucleosides were condensed with Fmoc-4-O-methyl-L-tyrosine and subsequently deprotected to give the target compounds 17 and 18. Compound 3 is converted into its glycosyl bromide 4 in quantitative yield on treatment with trimethylsilyl bromide, and reacted with the sodium salt of 6-dimethylaminopurine to give the corresponding protected N-7 and N-9 α glycosyl nucleosides 7 and 8 in 34 and 39% yield, respectively. The 2'-deoxypuromycin is inactive against HIV-1 in MT-4 cells.
Synthesis of 6-Dimethylaminopurine 2',3'-Dideoxynucleosides
Motawia, Mohammed S.,El-Torgoman, Abdel Moneim,Pedersen, Erik B.
, p. 879 - 883 (2007/10/02)
The trimethylsilylated 6-dimethylaminopurine 1 was coupled with the 2',3'-dideoxyribose derivatives 2a, b and 7 by using trimethylsilyl triflate as catalyst to yield the corresponding nucleosides 3a, b, 4a, b and 8, which were appropriately deprotected to give the desired nucleosides 5a, b and 9 as well as the related α-isomers 6a, b and 10.The 2-deoxyribose derivative 12 was mesylated at the 3'-O-position to give 13 which was coupled similarly with 1 to yield compound 14 and its α-anomer 15.Compounds 14 and 15 were treated with tetrabutylammonium fluoride to give the desired 2',3'-didehydro-2',3'-dideoxynucleoside analogue 16 and its α-anomer 17. --- Key Words: Nucleosides, convergent synthesis / Nucleosides, 2',3'-dideoxy- / Nucleosides, 2',3'-didehydro- / Adenine, N6,N6-dimethylnucleosides
