Hydrochloric Acid → (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

HRID 258217Notes

Reaction equation

[CH:1]1[C:2]([C:10]([O:12][C@@H:13]2[O:18][C@@H:17]3[CH2:19][O:20]C(C4C=C(O)C(O)=C(O)C=4C4C(O)=C(O)C(O)=CC=4C([O:40][C@@H:15]([C@@H:16]3[OH:44])[C@H:14]2[OH:45])=O)=O)=[O:11])=[CH:3][C:4](O)=[C:5]([OH:8])[C:6]=1[OH:7].Cl>>[CH:1]1[C:6]([OH:7])=[C:5]([OH:8])[C:4]2[O:12][C:10](=[O:11])[C:2]3=[CH:1][C:6]([OH:7])=[C:5]([OH:8])[C:4]4[O:12][C:10](=[O:11])[C:2]=1[C:3]=2[C:3]=43.[O:12]=[CH:13][C@@H:14]([C@H:15]([C@@H:16]([C@@H:17]([CH2:19][OH:20])[OH:18])[OH:44])[OH:40])[OH:45]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 73568β-D-Glucopyranose, cyclic 3,6-(4,4′,5,5′,6,6′-hexahydroxy[1,1′-biphenyl]-2,2′-dicarboxylate) 1-(3,4,5-trihydroxybenzoate)

Product 2

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

HCID 5281855Ellagic acid

Procedure

Hydrolysis of corilagin with 0.1N HCl was performed for 1 hr and the solution was chromatographed over Sephadex LH-20 using (H2O -MeOH, 10:0-3:7) to give ellagic acid (1H-NMR in DMSO-d6 : δ 7.45, 2H, s), gallic acid (1H-NMR in acetone-d6 : δ 7.14, 2H, s) and glucose (Rf=0.45, cellulose plate, n-BuOH:pyridine:H2O=6:4:3, under aniline hydrogen phthalate spray as brown spot)

Workup

customthe solution was chromatographed over Sephadex

Sources & evidence

ORD record: ord-9766c26c955c4a4f9c360b4518460324
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05266319

Reaction notes

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