Highly Stereoselective β-Anomeric Glycosidation of a 2‘-Deoxy Syn-5‘-Configured 4‘-Spironucleoside

A direct enantioselective pathway that delivers exclusively the beta-anomer of a 4'-spironucleoside has been successfully developed. The key starting material is the enantiomerically pure dihydroxy lactone 19, which has proven amenable to conversion to glycal 22 via the chloro acetonide. This i...

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Veröffentlicht in:	Journal of organic chemistry 2006-02, Vol.71 (4), p.1647-1652
Hauptverfasser:	DONG, Shuzhi, PAQUETTE, Leo A.
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Glycosylation Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Lactones - chemistry Nucleosides - chemical synthesis Organic chemistry Preparations and properties Spiro Compounds - chemical synthesis Stereoisomerism Thymine - chemistry
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Beschreibung
Zusammenfassung:	A direct enantioselective pathway that delivers exclusively the beta-anomer of a 4'-spironucleoside has been successfully developed. The key starting material is the enantiomerically pure dihydroxy lactone 19, which has proven amenable to conversion to glycal 22 via the chloro acetonide. This intermediate is then capped as the 3,5-O-(tetraisopropyldisiloxane-1,3-diyl) glycal. The latter can enter into N-iodosuccinimide-promoted glycosidation with persilylated thymine. Only the beta anomer is formed. Ensuing deiodination and desilylation proceed quantitatively to furnish the targeted, previously elusive anomer.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo052324h