D-(-)-Fructose → Sorbitol

HRID 904981Notes

Reaction equation

[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[O:13]=[CH:14][C@H:15]([C@H:17]([C@@H:19]([C@H:21]([CH2:23][OH:24])[OH:22])[OH:20])[OH:18])[OH:16].OCC([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.O=C[C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>>[OH:12][CH2:11][C@@H:9]([C@H:7]([C@@H:5]([C@@H:3]([CH2:2][OH:1])[OH:4])[OH:6])[OH:8])[OH:10].[CH2:23]([OH:24])[C@H:21]([C@H:19]([C@@H:17]([C@@H:15]([CH2:14][OH:13])[OH:16])[OH:18])[OH:20])[OH:22]

Participants

Reactant 5

HCID 5984D-(-)-Fructose

HCID 80127L-Gulose

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal3×

HCID 111112aldehydo-L-idose

HCID 161658Demannose

Product 2

HCID 5780Sorbitol

HCID 6251Mannitol

Procedure

A method for producing L-sugars including L-idose and L-gulose as well as D-fructose from D-glucose. The method comprises epimerizing D-glucose to a mixture of D-glucose and D-mannose, hydrogenating the mixture in a fixed catalyst bed to provide D-sorbitol and D-mannitol, separating the D-mannitol by fractional crystallization, oxydizing separately the D-sorbitol and D-mannitol to provide L-sorbose and D-fructose, respectively; and racemizing the L-sorbose in a weak alkaline solution to provide a mixture of L-sorbose, L-idose and L-gulose, and precipitating the remaining L-sorbose with a dilute lime solution. The unconverted L-sorbose is recovered and recycled.

Sources & evidence

ORD record: ord-deb1b36d1cae443492fa715e599cac0f
Source dataset: uspto-grants-1983_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04421568

Reaction notes

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