Phenylboronic Acid → D-(-)-Fructose

HRID 1752174

Reaction equation

HRID 1752174 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].C(C1C=CC=CC=1B(O)O)(O)=O.C1(B(O)O)C=CC=CC=1.CCN1C=[N+](C)C=C1.[Cl-]>CC(N(C)C)=O>[OH:1][CH2:2][C:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])=[O:4]

Participants

6

Reactant 4

HCID 66827Phenylboronic AcidHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 27339852-(Dihydroxyboranyl)benzoic acidHCID 27341601-Ethyl-3-methylimidazolium chloride

Product 1

HCID 5984D-(-)-Fructose

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

Glucose (49.5 mg, 275 μmol), 2-carboxyphenylboronic acid (45.9 mg, 277 μmol) or other phenylboronic acid (as indicated) and MgO (36.6 mg, 908 μmol) were mixed in DMA or [EMIM]Cl (500 mg). The reaction mixture was heated at 120° C. for 4 h. At 1-h intervals, aliquots of the reaction mixture were removed for analysis by HPLC.

Workup

  1. customAt 1-h intervals, aliquots of the reaction mixture were removed for analysis by HPLC

Sources & evidence

ORD record
ord-e538e07c080242878556e2b688c7b27b
Source dataset
uspto-grants-2015_10
Patent number
US09162999B2

Linked notes

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