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Nucleoside und Nucleotide. Teil 10. Synthese von Thymidylyl-(3′-5′) -thymidylyl-(3′-5′)-1-(2′-desoxy-β-D-ribofuranosyl)-2(1 H)-pyridon

✍ Scribed by Nico Cerletti; Christoph Tamm

Publisher
John Wiley and Sons
Year
1977
Tongue
German
Weight
924 KB
Volume
60
Category
Article
ISSN
0018-019X

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✦ Synopsis

Nucleosides and Nucleotides. Part 10. Synthesis of Thymidylyl-(3'-5')-thymidylyl-(3'-5')-l-(2'-deoxy-~-D-ribofuranosyl)-2(1 H)-pyridone Summary The synthesis of 5'-O-monomethoxytritylthymidylyl-(3'-5')-thymidylyl-(3'-5')-I -(2'deoxy-B-~-ribofuranosyl)-2(1 H)-pyridone ((MeOTr)TdpTdpnd, 5) and of thymidylyl-(3'-5')-thymidylyl-(3'-5')-1-(2'-deoxy-~-~-ribofuranosyl)-2( 1 H)-pyridone (TdpTdpnd, 11) by condensing (MeOTr)TdpTd (3) and pnd(Ac) (4) in the presence of DCC in abs. pyridine is described. Condensation of ( )TdpTdp (6) with ud(Ac) (7) did not yield the desired product 5 because compound 6 formed the 3'-pyrophosphate. The removal of the acetyl-and p-methoxytrityl protecting group was effected by treatment with cone. ammonia solution at room temperature, and acetic acid/ pyridine 7: 3 at IOO", respectively. Enzymatic degradation of the trinucleoside diphosphate l l with phosphodiesterase I and I1 yielded Td, pTd and pnd, Tdp and n d , respectively, in correct ratios.

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