Reaction SMILES: [C:1]([CH2:4][CH2:5][CH2:6][N:7]1[C:11]2=[N:12][CH:13]=[CH:14][C:15]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:20][CH:19]=3)=[C:10]2[C:9]([O:31][C@@H:32]2[O:58][C@H:57]([CH2:59][O:60][C:61](=[O:66])[C:62]([CH3:65])([CH3:64])[CH3:63])[C@@H:49]([O:50][C:51](=[O:56])[C:52]([CH3:55])([CH3:54])[CH3:53])[C@H:41]([O:42][C:43](=[O:48])[C:44]([CH3:47])([CH3:46])[CH3:45])[C@H:33]2[O:34][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[N:8]1)([OH:3])=O.C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C.C(=O)([O-])O.[NH4+:86].Cl>CN(C)C=O.N1C=CC=CC=1>[C:1]([CH2:4][CH2:5][CH2:6][N:7]1[C:11]2=[N:12][CH:13]=[CH:14][C:15]([CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][C:25](=[O:30])[C:26]([CH3:28])([CH3:27])[CH3:29])=[CH:22][CH:23]=3)=[C:10]2[C:9]([O:31][C@@H:32]2[O:58][C@H:57]([CH2:59][O:60][C:61](=[O:66])[C:62]([CH3:64])([CH3:65])[CH3:63])[C@@H:49]([O:50][C:51](=[O:56])[C:52]([CH3:54])([CH3:53])[CH3:55])[C@H:41]([O:42][C:43](=[O:48])[C:44]([CH3:45])([CH3:47])[CH3:46])[C@H:33]2[O:34][C:35](=[O:40])[C:36]([CH3:37])([CH3:38])[CH3:39])=[N:8]1)(=[O:3])[NH2:86]
Reactant: CC(C)(C)C(=O)OC[C@H]1O[C@@H](Oc2nn(CCCC(=O)O)c3nccc(CCc4ccc(OC(=O)C(C)(C)C)cc4)c23)[C@H](OC(=O)C(C)(C)C)[C@@H](OC(=O)C(C)(C)C)[C@@H]1OC(=O)C(C)(C)C
Reactant: [NH4+]
Agent: CC(C)(C)OC(=O)OC(=O)OC(C)(C)C
Agent: Cl
Agent: O=C([O-])O
Solvent: c1ccncc1
Solvent: CN(C)C=O
Product: CC(C)(C)C(=O)OC[C@H]1O[C@@H](Oc2nn(CCCC(N)=O)c3nccc(CCc4ccc(OC(=O)C(C)(C)C)cc4)c23)[C@H](OC(=O)C(C)(C)C)[C@@H](OC(=O)C(C)(C)C)[C@@H]1OC(=O)C(C)(C)C
Temperature: 25 °C
Reaction time: 3 h
Yield: 84.3 %

Procedure:
To a solution of 1-(3-carboxypropyl)-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-4-[2-(4-pivaloyloxyphenyl)-ethyl]-1H-pyrazolo[3,4-b]pyridine (95 mg) in N,N-dimethylformamide (2 mL) were added di (tert-butyl)dicarbonate (90 mg), pyridine (0.033 mL) and ammonium hydrogen carbonate (33 mg), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into 0.5 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, a saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/2-dichloromethane/methanol=15/1) to give 1-(3-carbamoylpropyl)-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-4-[2-(4-pivaloyloxyphenyl)ethyl]-1H-pyrazolo[3,4-b]pyridine (80 mg). This material was dissolved in methanol (2 mL). To the solution was added sodium methoxide (0.05 mL), and the mixture was stirred at 60° C. overnight. To the reaction mixture was added acetic acid (0.025 mL), and the resulting mixture was concentrated under reduced pressure. The residue was dissolved in a saturated aqueous potassium carbonate solution, and the solution was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) to give the product. The product was further purified by column chromatography on silica gel (eluent: dichloromethane/methanol =5/1−3/1) to give the title compound (23 mg).