Lactic Acid → (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

반응식

C(=O)(O)O.[C:5]([OH:10])(=O)[C:6](O)=[O:7].C(O)(=O)C(CO)O.C(O)(=O)CO.C(O)(=O)C(C)O.[O:29]=[C:30](O)[C@@H:31]([C@@H:33]([CH2:35][OH:36])[OH:34])[OH:32]>>[O:29]=[CH:30][C@@H:31]([C@H:33]([C@@H:35]([C@@H:6]([CH2:5][OH:10])[OH:7])[OH:36])[OH:34])[OH:32]

참가 물질

반응물 6

HCID 612Lactic Acid

HCID 752Glyceric acid

HCID 757Glycolic Acid

HCID 767Carbonic Acid

HCID 971Oxalic Acid

HCID 2781043Erythronic acid

생성물 1

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal수율 25%

실험 절차

This type of alkaline oxidative degradation, which is 25 effective both on hemiacetal functions and on ketone functions, also entails the formation of by-products such as, in particular, carbonic acid, oxalic acid, glyceric acid, glycolic acid, lactic acid, erythronic acid and, of course, fornic acid, which are obtained in a molar yield of about 25% from glucose when the alkalinity conditions are such that they allow a 75% yield of arabinonate. Formic acid is always produced in yields close to 100% of the stoichiometry.