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 1673301Notes

Reaction equation

HRID 1673301 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-b6e9883a60cb437aa72fe684f5ea3e1c
Source dataset
uspto-grants-2011_08
Patent number
US07998975B2

Reaction notes

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