Acetate → Penta-O-galloyl-beta-D-glucose

HRID 467186

Reaktionsgleichung

Reaktionsgleichung von HRID 467186
C1C(O)=C(O)C(O)=CC=1C([O:12][C:13]1[CH:14]=[C:15]([C:21]([O:23][CH2:24][C@H:25]2[O:30][C@@H:29]([O:31][C:32]([C:34]3[CH:35]=[C:36]([OH:53])[C:37]([OH:52])=[C:38]([O:40]C(C4C=C(O)C(O)=C(O)C=4)=O)[CH:39]=3)=[O:33])[C@H:28]([O:54][C:55]([C:57]3[CH:58]=[C:59]([OH:76])[C:60]([OH:75])=[C:61]([O:63]C(C4C=C(O)C(O)=C(O)C=4)=O)[CH:62]=3)=[O:56])[C@@H:27]([O:77][C:78]([C:80]3[CH:81]=[C:82]([OH:99])[C:83]([OH:98])=[C:84]([O:86]C(C4C=C(O)C(O)=C(O)C=4)=O)[CH:85]=3)=[O:79])[C@@H:26]2[O:100][C:101]([C:103]2[CH:104]=[C:105]([OH:122])[C:106]([OH:121])=[C:107]([O:109]C(C3C=C(O)C(O)=C(O)C=3)=O)[CH:108]=2)=[O:102])=[O:22])[CH:16]=[C:17]([OH:20])[C:18]=1[OH:19])=O.C([O-])(=O)C>CO>[C:32]([O:31][C@@H:29]1[O:30][C@H:25]([CH2:24][O:23][C:21](=[O:22])[C:15]2[CH:14]=[C:13]([OH:12])[C:18]([OH:19])=[C:17]([OH:20])[CH:16]=2)[C@@H:26]([O:100][C:101](=[O:102])[C:103]2[CH:108]=[C:107]([OH:109])[C:106]([OH:121])=[C:105]([OH:122])[CH:104]=2)[C@H:27]([O:77][C:78](=[O:79])[C:80]2[CH:85]=[C:84]([OH:86])[C:83]([OH:98])=[C:82]([OH:99])[CH:81]=2)[C@H:28]1[O:54][C:55](=[O:56])[C:57]1[CH:62]=[C:61]([OH:63])[C:60]([OH:75])=[C:59]([OH:76])[CH:58]=1)(=[O:33])[C:34]1[CH:39]=[C:38]([OH:40])[C:37]([OH:52])=[C:36]([OH:53])[CH:35]=1

Komponenten

4

Edukt 2

HCID 175AcetateHCID 16129778Tannic Acid

Produkt 1

HCID 65238Penta-O-galloyl-beta-D-glucoseAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To 1 g of tannic acid according to Japanese Pharmacopoeia (available from Iwaki Seiyaku Co., Ltd.), there were added 50 ml of methanol and 25 ml of acetate buffer (pH 5.5) and the resultant mixture was stirred at 50° C. for 18 hours. After distilling off methanol under a reduced pressure, the residue was extracted three times with ethyl acetate and then the solvent was distilled off under a reduced pressure. This crude product was fractionated by HPLC (YMC-PACK, D-ODS-5 20×250 mm; eluent=methanol: tetrahydrofuran: phosphate buffer (pH 4.5)=3:1:7) to obtain 282 mg of 1,2,3,4,6-penta-O-galloyl-β-D-glucose.

Aufarbeitung

  1. distillationAfter distilling off methanol under a reduced pressure
  2. extractionthe residue was extracted three times with ethyl acetate
  3. distillationthe solvent was distilled off under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-680b998af7df428593559b27c77e324e
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05159069

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