FORMATION OF 3-OCTULOSES BY A SELF-ALDOL REACTION OF D-ERYTHROSE

Article abstract of DOI:10.1016/S0008-6215(00)80987-8

When kept at 105 deg C for 2.5 h, weakly alkaline, syrupy D-erythrose was readily converted into a mixture containing mainly D-glycero-tetrulose, the previously unknown β-D-altro-L-glycero-3-octulofuranose (2), and α-D-gluco-L-glycero-3-octulopyranose, which were isolated as the corresponding acetates.Treatment of 2 with Dowex 50 (H+) resin yielded 3,8-anhydro-β-D-altro-L-glycero-octulopyranose, identified as its acetate.Previous discrepancies in the <α>D values for D-erythrose appear partly to originate in the self-aldol reaction.The dimerisation of D-erythrose 4-phosphate is also described.