Alicyclic carbohydrates. XXXIII. Epimerization of pseudo-.alpha.-DL-: talopyranose to pseudo-.alpha.-DL-galactopyranose. Proton magnetic resonance studies

Current Synthetic Approaches to the Synthesis of Carbasugars from Non-Carbohydrate Sources

“…The term "carbohydrate mimetic" is used frequently to refer to any carbohydrate derivative or other compound that has multiple hydroxy groups and thereby resembles a saccharide. Between 1966 and1968, the research group of McCasland developed a series of derivatives in which the ring oxygen of a monosaccharide was replaced by a methylene group; these authors neologized the term "pseudo sugars" for this family of compounds, though such compounds are currently called "carbasugars" (Scheme 1) [8,9]. The researchers hypothesized that the structural resemblance of carbasugars to the original sugars would enable their identification by enzymes or other biological systems in place of the related true sugars.…”

Gram-scale carbasugar synthesis via intramolecular seleno-Michael/aldol reaction

“…These compounds are structurally related to carbohydrates where the ring oxygen is replaced with a methylene group. 1,2 Carbasugar fragments have been found in various natural products. 3,4 The structural similarity of carbasugar fragments to conventional monosaccharides suggests that they are likely to bind and inhibit the same protein targets.…”

Synthesis and biological evaluation of phosphoramidate prodrugs of two analogues of 2-deoxy-d-ribose-1-phosphate directed to the discovery of two carbasugars as new potential anti-HIV leads

“…The term 'carbasugar' refers to a family of compounds in which the oxygen atom of the furanose sugar ring has been replaced by a methylene group. [9][10][11] Carbasugars are chemically more stable towards degradation than their sugar analogues 12 but at the same time, due to their resemblance to natural sugars, they may be still recognized by the same enzymes. 12 It is well known that the therapeutic potential of drugs bearing a phosphate moiety is decreased because of the negative charges of the phosphate group at physiological pH.…”