4-{2-[4-(3-Benzyloxypropoxy)phenyl]ethyl}-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazolo-[3,4-b]pyridine → HCID 67340558, compound

HRID 2223955Notes

Reaction equation

HRID 2223955 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]3[NH:27][N:28]=[C:29]([O:30][C@@H:31]4[O:57][C@H:56]([CH2:58][O:59][C:60](=[O:65])[C:61]([CH3:64])([CH3:63])[CH3:62])[C@@H:48]([O:49][C:50](=[O:55])[C:51]([CH3:54])([CH3:53])[CH3:52])[C@H:40]([O:41][C:42](=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44])[C@H:32]4[O:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])[C:22]=23)=[CH:15][CH:14]=1)C1C=CC=CC=1>O1CCCC1.CO.[C].[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]3[NH:27][N:28]=[C:29]([O:30][C@@H:31]4[O:57][C@H:56]([CH2:58][O:59][C:60](=[O:65])[C:61]([CH3:64])([CH3:63])[CH3:62])[C@@H:48]([O:49][C:50](=[O:55])[C:51]([CH3:52])([CH3:53])[CH3:54])[C@H:40]([O:41][C:42](=[O:47])[C:43]([CH3:46])([CH3:45])[CH3:44])[C@H:32]4[O:33][C:34](=[O:39])[C:35]([CH3:36])([CH3:37])[CH3:38])[C:22]=23)=[CH:17][CH:18]=1

Participants

5

Reactant 1

HCID 866143864-{2-[4-(3-Benzyloxypropoxy)phenyl]ethyl}-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazolo-[3,4-b]pyridine

Product 1

HCID 67340558HCID 67340558, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-{2-[4-(3-Benzyloxypropoxy)phenyl]ethyl}-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazolo-[3,4-b]pyridine (0.4 g) was dissolved in a mixed solvent of tetrahydrofuran (6 mL) and methanol (6 mL). To the solution was added 10% palladium-carbon powder (160 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 3 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (0.36 g).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d0f271824ce34b7c8bb9ae1f0f8e3547
Source dataset
uspto-grants-2008_05
Patent number
US07375113B2

Reaction notes

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