5-Thio sugar nucleosides, synthesis

Reist, E J, Eisher, L V, Goodman, L, Thio Sugars. Synthesis of the adenine nucleosides of 4-thio-D-xylose and 4-thio-D-arabinose, J. Org. Chem., 33, 189-192, 1968. 

The synthesis of purine and pyrimidine 2 -deoxynucleosides from a 1,2-dithio-sugar precursor is noted in Chapter 21, which also refers to the alkylation of seleno- and thio-substituted nucleosides using a mixture of a dialkyl disulphide (or diselenide) and tributylphosphine in DMF. Other thio-sugar derivatives are mentioned in Chapter 12. 

This article collates information on the reactivity of sugar isothiocyanates and isomeric thiocyanates, and illustrates some of the chemical properties that have contributed to the synthesis of nucleoside analogs,1719 and thio and deoxy sugars. 

In an article that collates information not extensively treated before, Z. J. Witczak (West Lafayette) describes the synthesis, chemistry, and preparative applications of monosaccharide thiocyanates and isothiocyanates the thiocyanate anion is an ambident nucleophile of great synthetic versatility in approaches to nucleoside analogs and to thio and deoxy sugars. 

A stereocontrolled general synthesis of C-nucleosides from non-carbohydrate materials has been described, illustrated in Scheme 9 for pseudo-uridine derivatives (69) (R = H, Me, CsHn, or Ph R = H) a branched-chain sugar derivative (69) (R = R = Me) was analogously prepared. 2-Thio-pseudouridine and pseudoisocytidine were also obtained from the intermediate (70) (R = R = H) using thiourea and guanidine respectively in place of urea, and this intermediate was also converted to the maleimido C-nucleoside, showdomycin. ... 

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