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

HRID 467186

반응식

HRID 467186 반응식
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

참가 물질

4

반응물 2

HCID 175AcetateHCID 16129778Tannic Acid

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-680b998af7df428593559b27c77e324e
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05159069

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