1,3-dioxolane C-nucleosides: Asymmetric synthesis of four stereoisomers of 2-[2-(hydroxymethyl)-1,3-dioxolan-5-yl]-1,3-thiazole-4-carboxamide

Article abstract of DOI:10.1016/00404-0399(50)17638-

Asymmetric synthesis of four novel C-nucleosides, (2′R,5′R)-, (2′S,5′R)-, (2′S,5′S)- and (2′R,5′S)-2-[2-hydroxymethyl)-1,3-dioxolan-5-yl]-1,3-thiazole-4- carboxamide has been accomplished by the condensation of key intermediates, 2-(1R- and 1S-glycol-1-yl)-4-ethoxycarbonyl-1,3-thiazole with 2-benzoyloxy acetaldehyde dimethyl acetal.