108392-14-9Relevant articles and documents
Regioselective benzylation of pentitols, tetritols, and some hexitols via their stannyl ether derivatives: Versatile synthesis of monobenzylalditols
Halila, Sami,Benazza, Mohammed,Demailly, Gilles
, p. 467 - 483 (2001)
The xylitol, ribitol and D-arabinitol were transformed into their tributylstannyl ether derivatives by reaction with bis-tributyltin oxide [(nBu3Sn)2O I] and azeotropic removal of water. Subsequent benzyl etherification, using BnBr with solvent or under free solvent conditions, led regioselectively to primary mono-O-benzylalditol derivatives in satisfactory yields for a direct regioselective synthesis (~ 52%). This etherification when applied to tetritols and some hexitols exhibits similar behaviour. With pentitols, an analogous study carried out with the n-dibutyltin oxide [nBu2SnO (II)] as the activating reagent showed contrasting results as regards regioselectivity.
Efficient asymmetric organocatalytic formation of erythrose and threose under aqueous conditions
Burroughs, Laurence,Vale, Matthew E.,Gilks, James A. R.,Forintos, Henrietta,Hayes, Christopher J.,Clarke, Paul A.
supporting information; experimental part, p. 4776 - 4778 (2010/09/05)
Esters of proteinogenic amino acids efficiently catalyse the formation of erythrose and threose under aqueous conditions in the highest yields and enantioselectivities yet reported. Remarkably while esters of (l)-proline yield (l)-carbohydrates, esters of (l)-leucine and (l)-alanine generate (d)-carbohydrates, offering the potential to account for the prebiotic link between natural (l)-amino acids and natural (d)-sugars.
EQUILIBRATION OF ALDITOL ANHYDRIDES IN ACETIC ACID
Wisniewski, Andrzej,Gajdus, Jerzy,Sokolowski, Janusz,Szafranek, Janusz
, p. 11 - 20 (2007/10/02)
Dehydration of pentitols in acetic acid containing an acidic catalyst parallels that in aqueous sulfuric acid; 1,4(2,5)-dehydration occurs with inversion of configuration at C-2 or C-4.Acetylated alditols undergo similar processes via intermediates having free hydroxyl groups.Configurational inversion of 1,4- or 1,5-anhydroalditols is attributed to intermediate acyloxonium ions that are also proposed as intermediates in the structural isomerisation.Drastic treatment of each alditol gives equilibrium mixtures.The equilibrium concentrations are used to calculate free-energy differences.