In 1984,Kazimierczuk, Zygmunt; Cottam, Howard B.; Revankar, Ganapathi R.; Robins, Roland K. published 《Synthesis of 2′-deoxytubercidin, 2′-deoxyadenosine, and related 2′-deoxynucleosides via a novel direct stereospecific sodium salt glycosylation procedure》.Journal of the American Chemical Society published the findings.Recommanded Product: 90213-66-4 The information in the text is summarized as follows:
A general and stereospecific synthesis has been developed for the direct preparation of 2′-deoxy-β-D-ribofurnaosylpurine analogs including 2′-deoxyadenosine derivatives The reaction of the Na salt of chloropyrrolo[2,3-d]pyrimidines I (R = H, Cl) with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranose (II) provided the corresponding N-1 2′-deoxy-β-D-ribofuranosyl blocked derivatives which, on ammonolysis, gave 2′-deoxytubercidin (III, R = H) and 2-chloro-2′-deoxyrubercidin (III, R = Cl), resp., in good yields. This glycosylation also readily proceeds in the presence of a 2-methylthio group. Application of this glycosylation procedure to 4,6-dichloroimidazo[4,5-c]pyridine, 6-chloropurine, 2,6-dichloropurine, and 4-chloropyrazolo[3,4-d]pyrimidine gave 2-chloro-2′-deoxy-3-deazaadenosine, 2′-deoxyadenosine, 2-chloro-2′-deoxyadenosine, and 4-amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)pyrazolo[3,4-d]pyrimidine, resp. Similarly, glycosylation and ammonolysis of 4,6-dichloro-1H-pyrrolo[3,2-c]pyridine gave 4,6-dichloro-1-(2-deoxy-β-D-erythro-pentofuranosyl)pyrrolo[3,2-c]pyridine. This stereospecific attachment of the 2-deoxy-β-D-ribofuranosyl moiety appears to be due to a Walden inversion at the C-1 carbon of II. The results came from multiple reactions, including the reaction of 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine(cas: 90213-66-4Recommanded Product: 90213-66-4)
2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine(cas: 90213-66-4) belongs to pyrimidine. Pyrimidine nucleotide derivatives have a wide range of biological applications. For example, pyrimidine derivatives are useful in DNA repair studies involving cancer and epigenetics. Recommanded Product: 90213-66-4
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia