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A reaction of DBU promoted ring opening in nucleoside‐3'‐O‐ and nucleoside‐5'‐O‐(2‐thio‐4,4‐pentamethylene‐1,3,2‐oxathiaphospholane) monomers with a pyrophosphate or a methylenediphosphonate anion proceeds with substantial loss of stereoselectivity. Depending on the absolute configuration of the phosphorus atom, so far widely accepted the stereoretentive mechanism of condensation is accompanied by...
A method for stereocontrolled chemical synthesis of P‐substituted nucleoside 5′‐O‐phosphorothioates has been elaborated. Selected 3′‐O‐acylated deoxyribonucleoside‐ and 2′,3′‐O,O‐diacylated ribonucleoside‐5′‐O‐(2‐thio‐4,4‐pentamethylene‐1,3,2‐oxathiaphospholane)s were chromatographically separated into P‐diastereomers. Their reaction with anions of phosphorus‐containing acids was highly stereoselective...
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