Gluconic Acid → D-Arabitol

Reaktionsgleichung

[O:1]=[CH:2][C@H:3]([C@@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].O=C(O)[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>>[CH2:2]([OH:1])[C@H:3]([C@@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4]

Komponenten

Edukt 3

HCID 10690Gluconic Acid

HCID 66308D-Arabinose

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Produkt 1

HCID 94154D-Arabitol

Versuchsvorschrift

An alternative synthesis of D-arabinose consists in the oxidative degradation of gluconic acid, extensively described by Ruff in Berichte der Deutschen Chemischen Gesellschaft 32 (1899) 553-554. However, starting from glucose a minimum of three reaction steps are required to obtain arabinitol.