By Tohru Ueda (auth.), Leroy B. Townsend (eds.)
The current quantity is the 1st of a projected four-volume treatise. This quantity comprises the subsequent chapters: "Synthesis and response of Pyrimidine Nucleosides," "Synthesis and homes of Purine Nucleosides and Nucleotides," and "Synthesis and houses of Oligonucleotides." those 3 chapters have been chosen for inclusion in quantity I as the components have supplied the root and impetus for the initiation and improvement of the opposite parts of study, that allows you to be defined in next volumes. each one bankruptcy is quite finished in nature and will supply a prepared reference resource for not just the amateur but in addition the skilled investigator or researcher. The chapters were ready via authors with substantial adventure in every one specific sector of study, and this has ended in a lucid presentation of every well-defined region. those volumes have been designed with medicinal chemists, medicinal natural chemists, natural chemists, carbohydrate chemists, actual chemists, and organic chemists in brain. although, end result of the large contemporary curiosity during this learn zone as a result of the organic and chemotherapeutic overview of nucleosides and nucleotides as anticancer, antiviral, and antiparasitic brokers, those volumes must also be necessary additions to the libraries of virologists, biochemical pharmacologists, oncologists, and pharmacologists. we wish to thank the authors for his or her enthusiasm and assist in making those volumes on hand to the medical community.
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Extra resources for Chemistry of Nucleosides and Nucleotides: Volume 1
227) Styrene derivatives are also coupled with mercuri-uridine nucleosides and nucleotides by Pd(I1) to give the 5-styryl derivatives. (228) The preparation of 5-hydroxymethyl-2' -deoxyuridine 5'-phosphate labeled at the 5-hydroxymethyl carbon with 13C or 14C was accomplished by using the labeled styrene in the above reaction, followed by oxidative cleavage of the styrene function with osmium tetroxide-sodium perchlorate and successive borohydride reduction of the 5-formyl group. J O~f';I dR, 80 81 82 \~------------------~!
The reaction of 5-chloromercuricytidines with methyl acrylate in the presence of Li2 PdCl 4 gave the 5-(E)-acrylate (78). (234) Treatment of 5-chloromercuri-2'-deoxyuridine with substituted iodobenzenes in the presence of Li2 PdCl 4 afforded the 5-phenyluridine derivatives in low yields. (235) The conversion of 5-iodopyrimidine nucleosides, in place of the 5-mercuri derivatives, to the 5-alkyl derivatives has also been accomplished by a metalmediated reaction. Treatment of 3',5'-di-O-acetyl-2'-deoxy-5-iodouridine with iodotrifluoromethane in the presence of copper powder gave 5-trifluoromethyl-2'- Synthesis and Reaction of Pyrimidine Nucleosides 15 deoxyuridine (83),(236) an active antitumor nucleoside.
250) Although Pichat el al. observed that the lithiation of fully trimethylsilylated uridine by butyllithium occurs both at the 5 and 6 positions, (251) Tanaka el al. found a selective alkylation via the 6-lithiation. (252) Similarly, the reaction of aromatic aldehydes with 2',3'-O-isopropylidene-5'-O-methoxymethyl-6-lithiouridine gave the 6-hydroxybenzyl derivative, which was converted to the 6-aroyl derivatives (88) by oxidation with manganese oxide. (253) The reaction of diphenyl disulfide with 6-lithiouridine gave the 6-phenylthiouridine.