Dihydroxyacetone → L-Fructose

HRID 1731866Notes

Reaction equation

[CH2:1]([OH:6])[CH:2]([OH:5])[CH:3]=[O:4].[OH:7][CH2:8][C:9](=[O:12])[CH2:10][OH:11]>>[OH:4][CH2:3][C:2]([C@@H:1]([C@H:8]([C@H:9]([CH2:10][OH:11])[OH:12])[OH:7])[OH:6])=[O:5]

Participants

Reactant 2

HCID 670Dihydroxyacetone

HCID 751Glyceraldehyde

Product 1

HCID 5460024L-Fructose

Procedure

Recently, L-fructose was prepared by aldol condensation. See S. Morgenlie, Carbohydr. Res., 107 (1982) 137-141. DL-Glyceraldehyde condensed with 1,3-dihydroxy-2-propanone catalyzed by Dowex 1 (OH-) resin to give a hexulose mixture. Crystallization of the mixture from methanol yielded 54% of DL-fructose. Treatment of the DL-fructose mixture with baker's yeast gave a product from which 62% of 2,3:4,5-di-O-isopropylidene-β-L-fructopyranose was isolated after acetonation. When L-glyceraldehyde was used as starting material, 2,3:4,5-di-O-isopropylidene-β-L-fructopyranose was isolated in 60-65% yield after acetonation of the hexulose mixture.

Sources & evidence

ORD record: ord-ea84ad9db42840e09c649cf1307e4698
Source dataset: uspto-grants-1986_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04623721

Reaction notes

Loading…