Synthesis of C??5 and N??3 arenesulfenyl uridines. Preparation and properties of a new class of uracil protecting group

…, H Bazin, J Heikkilä, J Chattopadhyaya

Index: Welch, C. J.; Bazin, H.; Heikkila, J.; Chattopadhyaya, J. Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1985 , vol. 39, # 3 p. 203 - 212

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Citation Number: 20

Abstract

The nature and position of the ring substituent of an arenesulfenyl chloride control the regiospecific formation of either a C-5 substituted product, as in compounds 3a-3d, or a N-3 substituted product, as in compounds 2a-2c. Arenesulfenyl groups have been subsequently found to successfully protect the urethane function of the uracil residue as exemplified by the synthesis of 2'-0-methyl uridine and oligoribonucleotide building blocks.

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