Gluconic Acid → D-Arabitol

HRID 355499

Reaction equation

[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]

Participants

Reactant 3

HCID 10690Gluconic Acid

HCID 66308D-Arabinose

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

Product 1

HCID 94154D-Arabitol

Procedure

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.

Workup

customa minimum of three reaction steps

Sources & evidence

ORD record: ord-aa35eb104675409f9f0f65b0231ecdc1
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05831078

Linked notes

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