Uridine 5 -deoxy-5 -iodo-, preparation

A new synthesis of 3 -deoxy-3 -nitrothymidine involves displacement of an up -iodo-substituent by nitrite ion in DMSO in the presence of phloroglucinol. The (hydroxylamino)nucleoside 65 has been made by reduction of a C-3 nitrone with NaBHsCN, and related 0-alkylhydroxylamines were also described, prepared by reduction of O-alkyloximes. Similar O-alkyloximes at both C-2 and C-3 of uridine have been prepared as potential inhibitors of ribonucleoside diphosphate reductase. ... 

The RNA dinucleotide phosphorothiolate, 3 -(thioinosylyl)-(3 -5 )-uridine 59 (IspU) containing a 3 -S-phosphorothiolate linkage has been prepared from 9-(3-deoxy-3-iodo-P-D-xylofuranosyl)hypoxanthine using Arbuzov chemistry. IspU was found to be a substrate for several RNA hydrolysing enzymes and is also labile to acid, base and silver ions. The analogue has also been used to study the... 

Uridine has been converted in seven steps into 5 -amino-3, 5 -dideoxyuridine (66), related to the 4, 5 -unsaturated structure found in the mureidomycin antibiotics. Some 5 -Amino-5 -deoxy-5-iodo-pyrrolopyrimidine nucleosides such as 67 (X = Cl, NH2) have been prepared by sodium salt glycosylation procedures, and shown to be powerful adenosine kinase inhibitors. ... 

Verheyden and Moffatt have prepared l-(5-deoxypent-4-enofuranosyl) derivatives of uridine, thymidine, cytidine, and 2 -deoxycytidine by dehydrohalogen-ation of the acetylated 5 -deoxy-5 -iodo-nucleoside with either silver fluoride in pyridine or DBN (Scheme 89). ° Similar treatment of 3, 5 -dideoxy-3, 5 -di-iodothymidine (235) furnished the dihydrofuran derivative (236). Addition reactions of 4, 5 -unsaturated derivatives of nucleosides are mentioned in Chapter 21. 

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