ACYCLIC-SUGAR 6-CHLOROPURINE NUCLEOSIDE ANALOGS DERIVED FROM D-ALDOHEXOSES HAVING THE D-erythro STEREOCHEMISTRY AT C-4 AND C-5

Article abstract of DOI:10.1016/S0008-6215(00)80775-2

1-(6-Chloropurin-9-yl)-1-S-ethyl-1-thio-D-mannitol, 1-(6-chloropurin-9-yl)-1-S-ethyl-1-thio-D-altritol, and 1-(6-chloropurin-9-yl)-3-deoxy-1-S-ethyl-1-thio-D-arabino-hexitol were prepared by a new method of direct coupling of an acyclic-sugar derivative to the base.The coupling products were obtained as pairs of 1'-epimers.The epimeric mixture of D-manno derivatives was resolved by liquid chromatography, and the products were fully characterized.Glycosylation at N-9 of the purine ring was established by u.v. and (13)C-n.m.r. spectroscopy, and the chirality at C-1' by circular dichroism measurements.The conformations of the acyclic-sugar chains in solution were also examined.