Synthesis of 1,2-trans-related 1-thioglycoside esters

The extracellular polysaccharides of porphyridium cruentum and porphyridium aerugineum

Publisher Summary This chapter provides an overview of dithioacetals and their direct chemical transformations. Dithioacetals and their derivatives comprise the largest recorded class of acyclic carbohydrate derivatives. They are versatile intermediates in synthesis not only because a multitude of transformations are possible at the dithioacetal group, but also because all of the hydroxyl groups of the sugar chain are available for chemical transformation or selective protection. Of particular importance is the fact that they provide a route for kinetically controlled ring-closure of the sugar under neutral conditions by the action of mercury (II) salts, thus providing a useful route of access to furanosides. Although dithioacetals are odorless, an inherent practical disadvantage of their preparation is the generally disagreeable scent of the lower thiols. Furthermore, appended to this chapter is a set of tables that lists the melting points and specific rotations of sugar dithioacetals and certain derivatives.

Dithioacetals of Sugars

Trifluoroacetyl as an N-protective group in the synthesis of purine nucleosides of 2-amino-2-deoxy saccharides

Facile conversion of adenosine into new 2′-substituted-2′-deoxy-arabinofuranosyladenine derivatives: Stereospecific syntheses of 2′-azido-2′-deoxy-,2′-amino-2′- deoxy-, and 2′-mercapto-2′-deoxy-β-d-arabinofuranosyladenines

Shigeharu Inouye

Papers

Synthesis and spectral properties of cytosine nucleosides of 2-amino-2-deoxy-α-D-arabino-furanose and -pyranose

Four isomeric ethyl 1-thioglycosides from 2-amino-2-deoxy-D-arabinose.

Anomeric forms of 9-(2-amino-2-deoxy-d-xylofuranosyl)adenine

Synthesis of a cytosine nucleoside of 2-amino-2-deoxy-β-D-xylofuranose