105967-08-6Relevant articles and documents
Synthesis of cyclopentane analogs of (2'- and 3'-deoxy-erythro-pentofuranosyl and ribofuranosyl)-2-thiouracil nucleosides
Hronowski, Lucjan J. J.,Szarek, Walter A.
, p. 1620 - 1629 (2007/10/02)
Three new carbocyclic analogus of nucleosides having the 2-thiouracil base have been synthesized.The cyclopentyl groups in these nucleosides are (+/-)- (see 31), (+/-)- (see 32) and (+/-)- (see 33).The nucleosides were prepared by coupling the appropriate hydroxy derivatives of cis-3-aminocyclopentanemethanol with 3-ethoxypropenoyl isothiocyanate (21) followed by cyclization in 15 N aqueous ammonia to give the 2-thiouracil nucleosides.In addition a modified and shortenedsynthetic route is described for the synthesys of (+/-)-(1β,2α,3α,4β)-4-amino-2,3-dihydroxy-cyclopentanemethanol (19).The (1)H nmr spectra at 200 MHz of all of the synthetic intermediates, the 2-thiouracil nucleosides, and of the corresponding carbocyclic analogs of uracil nucleosides are discussed.It is shown that each nucleoside has a characteristically unique (1)H nmr spectrum and that in general the protons in the sulfur-containing compounds resonate at lower filds than those in the corresponding oxygen-containing compounds.The magnitude of this downfield shift is inversely related to the number of bonds separating a particular proton from the sulfur atom.