Equilibrium of α- and β-hydroxyls at the anomeric positionPotential competing inter-conversion betweenαandβformsinter-conversion between Pyranose and furanoseforms
Potential competing inter-conversion between α and β forms Equilibrium of α- and β-hydroxyls at the anomeric position inter-conversion between pyranose and furanose forms
Solubility: very polar in naturevery soluble in polar solvents, especiallywith possible H-bondingInsoluble in non-polar solvents for organicreactions, pdt purification and manipulationSelective protection of particularhydroxyl groups allows the regioselctiverxn of those unprotectedCommon starting point: protect themajority or even all of the free -OH
Solubility: very polar in nature very soluble in polar solvents, especially with possible H-bonding Insoluble in non-polar solvents for organic reactions, pdt purification and manipulation Selective protection of particular hydroxyl groups allows the regioselctive rxn of those unprotected Common starting point: protect the majority or even all of the free -OH
AcetalsEtherAcetylationNucleophilicEsteroxidationSubstitutionReduction
AcetylaKon Acetals Ether Ester Nucleophilic SubsKtuKon oxidaKon ReducKon
AcetalsAcetylationEtherNucleophilicEsteroxidationSubstitutionReduction
AcetylaKon Acetals Ether Ester Nucleophilic SubsKtuKon oxidaKon ReducKon
0000R-CXR-COC-RRCOHacyl halidecarboxylic acidanhydrideEsters: non-nucleophilic and stable to a wide range ofConditionsFrequentlyusedprotectgroupsLess polar than the corresponding alcohols
Esters:$non9nucleophilic$and$stable$to$a$wide$range$of$$ Condi,ons$ Frequently$used$protect$groups$ Less$polar$than$the$corresponding$alcohols$