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8-Aza-7-deaza-2′,3′-dideoxyguanosine: Deoxygenation of its 2′deoxy-β-D-ribofuranoside

✍ Scribed by Frank Seela; Hansjüegen Driller


Publisher
John Wiley and Sons
Year
1988
Tongue
German
Weight
353 KB
Volume
71
Category
Article
ISSN
0018-019X

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Synthesis of 8-Aza-1,3-dideaza-2′-deoxya
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## Abstract The synthesis of 8‐aza‐1,3‐dideaza‐2′‐deoxyadenosine (3a) as well as of 4‐ and 5,6‐substituted benzotriazole 2′‐deoxy‐β‐D‐ribonucleosides is described (__Schemes 1–3__). Glycosylation of benzotriazole anions is stereoselective in all cases (exclusive β‐D‐anomer formation), but regioisom

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The syntheses of 7-deaza-N6-methyladenine N9-(2'-deoxy-~-o-ribofuranoside) (2) as well as o f 8-aza-7-deaza-N6-methyladenine N8-and N9-(2'-deoxyribofuranosides) (3 and 4, resp.) are described. A 4,4'-dimethoxytritylation followed by phosphitylation yielded the methyl phosphoramidites 12-14. They wer

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## Abstract Nucleobase‐anion glycosylation of 2‐[(2‐methyl‐1‐oxopropyl)amino]imidazo[1,2‐__a__]‐1,3,5‐triazin‐4(8__H__)‐one (**6**) with 3,5‐di‐__O__‐benzoyl‐2‐deoxy‐2‐fluoro‐__α__‐D‐arabinofuranosyl bromide (**8**) furnishes a mixture of the benzoyl‐protected anomeric 2‐amino‐8‐(2‐deoxy‐2‐fluoro‐D

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Oligonucleotides containing 7-substituted 8-aza-7-deazaguanines ( 6-amino-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-ones) were prepared by automated solid-phase synthesis. A series of 7-alkynylated 8aza-7-deaza-2'-deoxyguanosines (see 4a ± d) were synthesized with the 7-iodonucleoside 3c as starting