2-(tert-butyldimethylsiloxy)thiophene: Application to total syntheses of both enantiomers of 2′,3′-dideoxy-4′-thiocytidine
Tetrahedron LettersPublished 1 March 1995
Gloria Rassu, Pietro Spanu, Luigi Pinna, Franca Zanardi, Giovanni Casiraghi
Citations28
SJR quartileQ3
SJR score0.33
SNIP0.43
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Abstract
Exploiting novel 2-(tert-butyldimethylsiloxy)thiophene (1, TBSOT) as versatile carbon nucleophile and both enantiomers of glyceraldehyde acetonide as chiral sources, an entry to both enantiomers of anti HIV-active 2′,3′-dideoxy-4′-thiocytidine 10 and ent-10 was devised and executed.
Keywords
ChemistryBiochemistry, Genetics and Molecular BiologyPharmacology, Toxicology and Pharmaceutics
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