Nucleoside, I1) Über Synthesen von O′‐Benzyl‐Derivaten des Uridins*
Herrn Prof. Dr. Hans Beyer zum 65. Geburtstag gewidmet.
Abstract
deDie Synthese verschiedener O′‐Benzyl‐uridin‐Derivate (9–11, 18–20, 22–27) wird beschrieben. In Benzol/Dioxan‐Gemischen lassen sich geeignet geschützte Uridin‐Abkömmlinge mit NaH als Base und Benzylhalogeniden in hohen Ausbeuten selektiv an den Ribose‐Hydroxylgruppen verähtern. Ein neues, der Tritylierungsreaktion vergleichbares Benzylierungsverfahren unter neutralen Bedingungen mittels p‐Methoxy‐benzychlorid/2‐tert.‐Butyl‐pyridin wird angegeben.
Abstract
enNucleosides, I1) Syntheses of O′‐Benzyl Derivatives of Uridine
The synthesis of various O′‐benzyl derivatives of uridine (9–11, 18–20, 22–27) is described. Benzylations of partially blocked uridine derivatives with NaH as base and benzyl halides in benzene/dioxan mixtures take place with high yields almost exclusively at the hydroxyl groups of the ribose moiety. A new method for benzylations under neutral conditions – analogous to the tritylation reaction – is described with p‐methoxybenzyl chloride and 2‐tert.‐butyl‐pyridine.
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