Acetic Acid → 3-(beta-D-Glucopyranosyloxy)-4-(2-phenylethyl)-1H-pyrazolo-[3,4-b]pyridine

HRID 2223950Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[NH:15][N:16]=[C:17]([O:18][C@@H:19]4[O:45][C@H:44]([CH2:46][O:47]C(=O)C(C)(C)C)[C@@H:36]([O:37]C(=O)C(C)(C)C)[C@H:28]([O:29]C(=O)C(C)(C)C)[C@H:20]4[O:21]C(=O)C(C)(C)C)[C:10]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].C(O)(=O)C>CO>[C@@H:19]1([O:18][C:17]2[C:10]3[C:11](=[N:12][CH:13]=[CH:14][C:9]=3[CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[NH:15][N:16]=2)[O:45][C@H:44]([CH2:46][OH:47])[C@@H:36]([OH:37])[C@H:28]([OH:29])[C@H:20]1[OH:21]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-(2-phenylethyl)-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazolo-[3,4-b]pyridine (0.26 g) in methanol (5 mL) was added sodium methoxide (28% methanol solution, 0.067 mL), and the mixture was stirred at 50° C. for 5 hours. To the reaction mixture was added acetic acid (0.04 mL), and the resulting mixture was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1) to give the title compound (91 mg)

Workup

customthe resulting mixture was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1)

Sources & evidence

ORD record: ord-f4f0bc7ee8864d6ca8ca0748c9fa1178
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375113B2

Reaction notes

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