The Application of Mitsunobu Cyclization for the Synthesis of 2′,3′-Dideoxy-C-Nucleosides Designed as Didanosine Analogues

被引：5

作者：

Tite, Tony ^{[1
]}

Lougiakis, Nikolaos ^{[1
]}

Skaltsounis, Alexios-Leandros ^{[2
]}

Marakos, Panagiotis ^{[1
]}

Pouli, Nicole ^{[1
]}

Tenta, Roxane ^{[3
]}

Balzarini, Jan ^{[4
]}

机构：

[1] Univ Athens, Dept Pharm, Div Pharmaceut Chem, GR-15771 Athens, Greece

[2] Univ Athens, Dept Pharm, Div Pharmacognosy, GR-15771 Athens, Greece

[3] Harokopio Univ, Dept Sci Nutr Dietet, Athens 17671, Greece

[4] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium

来源：

SYNLETT | 2009年 / 11期

关键词：

C-nucleosides; heterocycles; pyrazolo[3,4-c]pyridine; pyrazolo[4,3-b]pyridine; dideoxynucleosides; C-NUCLEOSIDE; ANTIVIRAL ACTIVITY; BINDING-PROPERTIES; GLUTAMIC-ACID; DNA; H-4-LIGANDS; GLYCOSIDES; FACILE;

D O I：

10.1055/s-0029-1217364

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of new 2',3'-dideoxy-C-nucleosides structurally related to didanosine has been achieved. Their preparation involved condensation of a Suitably substituted, lithiated 2- or 4-picoline with 2',3'-dideoxy-5'-benzylribonolactone, followed by borohydride reduction of the resulting hemiacetals, intramolecular Mitsunobu cyclization of the derived diols, formation of the pyrazolo[3,4-c] or [4,3-b]pyridine ring-system and Subsequent removal of the protecting groups.

引用

页码：1741 / 1744

页数：4

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