The Reaction of O-Benzylidene Sugars with N-Bromosuccinimide.: VI. A New Synthesis of 2′-Deoxyuridine and some of its Selectively Substituted Derivatives

Abstract

A new synthesis of 2′-deoxyuridine and its selectively substituted derivatives has been developed, based on the reaction of appropriately substituted 2′,3′-O-benzylideneuridines with N-bromosuccinimide (NBS). The preponderant products are uridines containing bromine and benzoate groups in the 2′- and 3′-positions respectively.

Synthesis of Two Stable Nitrogen Analogues of S-Adenosyl-l-methionine

“…Alternative protecting groups were then considered for the ribose moiety. 2‘,3‘- O,O -Benzylidene adenosine was converted into the 5‘- O -tosylate 16 , which was treated with liquid methylamine (Figure ), but the desired 5‘-methylamino compound 17a was only isolated as minor product. Unexpectedly, the major product (2:1 ratio) from this reaction (51% yield) was found to be a 5‘-dimethylamino derivative, shown to be 17b by NMR analysis and unambiguous synthesis.…”