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cis - and trans -Designations describe the geometrical relationship of triazolylmethyl (C-2) and oxymethyl (C-4) substituents, either on the same face (cis) or the opposite face (trans) of the dioxolane ring. While going from tosyl derivatives (11a ? d) all the way to itraconazole stereoisomers 1a ? h, the cis and trans relationship does not change. However, according to Cahn?Ingold?Prelog priority rules, the R and S notations corresponding to C-4 of the dioxolane ring do change. For example, cis -2 S,4 S tosylate derivative (11a) eventually leads to cis -2 S,4 R,2? S (1a) or cis -2 S,4 R,2? R (1b) itraconazole stereoisomers.
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cis-and trans -Designations describe the geometrical relationship of triazolylmethyl (C-2) and oxymethyl (C-4) substituents, either on the same face (cis) or the opposite face (trans) of the dioxolane ring. While going from tosyl derivatives (11a ? d) all the way to itraconazole stereoisomers 1a ? h, the cis and trans relationship does not change. However, according to Cahn?Ingold?Prelog priority rules, the R and S notations corresponding to C-4 of the dioxolane ring do change. For example, cis -2 S,4 S tosylate derivative (11a) eventually leads to cis -2 S,4 R,2? S (1a) or cis -2 S,4 R,2? R (1b) itraconazole stereoisomers.
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