Sodium Iodide → 1-(2-Benzyloxyethyl)-4-(2-phenylethyl)-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazolo[3,4-b]pyridine

HRID 1673300Notes

Reaction equation

HRID 1673300 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:48](=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50])[C@@H:36]([O:37][C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40])[C@H:28]([O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[C@H:20]4[O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[C:10]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:61][CH2:62][O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1.[I-].[Na+]>CC(C)=O>[CH2:64]([O:63][CH2:62][CH2:61][N:15]1[C:11]2=[N:12][CH:13]=[CH:14][C:9]([CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:10]2[C:17]([O:18][C@@H:19]2[O:45][C@H:44]([CH2:46][O:47][C:48](=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50])[C@@H:36]([O:37][C:38](=[O:43])[C:39]([CH3:40])([CH3:41])[CH3:42])[C@H:28]([O:29][C:30](=[O:35])[C:31]([CH3:32])([CH3:33])[CH3:34])[C@H:20]2[O:21][C:22](=[O:27])[C:23]([CH3:24])([CH3:25])[CH3:26])=[N:16]1)[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 673412974-(2-Phenylethyl)-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 673417671-(2-Benzyloxyethyl)-4-(2-phenylethyl)-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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 (98 mg) in acetone (4 mL) were added cesium carbonate (87 mg), benzyl 2-bromoethyl ether (0.032 mL) and a catalytic amount of sodium iodide, and the mixture was stirred at room temperature for 3 days. The reaction mixture was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/1) to give the title compound (0.11 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-33b8b17855ee4a9b86ee8564fc6be0e2
Source dataset
uspto-grants-2011_08
Patent number
US07998975B2

Reaction notes

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