6-Amino-2-(2-deoxy-β-D-ribofuranosyl)-2,5-dihydro-4H-pyrazolo-[3,4-d]-pyrimidin-4-one - CAS 109737-94-2
Category:
Nucleosides
Product Name:
6-Amino-2-(2-deoxy-β-D-ribofuranosyl)-2,5-dihydro-4H-pyrazolo-[3,4-d]-pyrimidin-4-one
Catalog Number:
109737-94-2
CAS Number:
109737-94-2
Molecular Weight:
267.24
Molecular Formula:
C10H13N5O4
COA:
Inquire
MSDS:
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Structure\Application:
2'-Deoxy-Nucleosides
Chemical Structure
CAS 109737-94-2 6-Amino-2-(2-deoxy-β-D-ribofuranosyl)-2,5-dihydro-4H-pyrazolo-[3,4-d]-pyrimidin-4-one

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Reference Reading


1.A new synthesis of certain 7-(beta-D-ribofuranosyl) and 7-(2-deoxy-beta-D-ribofuranosyl) derivatives of 3-deazaguanine via the sodium salt glycosylation procedure.
Gupta PK, Robins RK, Revankar GR. Nucleic Acids Res. 1985 Jul 25;13(14):5341-52.
A facile synthesis of 7-beta-D-ribofuranosyl-3-deazaguanine (1) and certain 8-substituted derivatives of 1 via the sodium salt glycosylation method has been developed. Glycosylation of the sodium salt of methyl 2-chloro(or methylthio)-4(5)-cyanomethylimidazole-5(4)-carboxylate (5 and 13b) with 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide (6) gave exclusively methyl 2-chloro(or methylthio)-4-cyanomethyl-1-(2,3, 5-tri-O-benzoyl-beta-D-ribofuranosyl)imidazole-5-carboxylate (7 and 14a), respectively. Ammonolysis of 7 and 14a provided 6-amino-2-chloro(or methylthio)-3-beta-D-ribofuranosylimidazo-[4,5-c]pyridin-4(5H)-one (11 and 17), which on subsequent dehalogenation (or dethiation) gave 1. Similarly, reaction of the sodium salt of 5 and 13b with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-alpha-D-erythro-pentofuranose (8), and ammonolysis of the glycosylated imidazole precursors (9 and 16) gave 6-amino-2-chloro(or methylthio)-3-(2-deoxy-beta-D-erythro-pentofuranosyl) imidazo[4,5-c]-pyridin-4(5H)-one (10a and 15), respectively.