Sodium Methoxide → β-D-Glucopyranoside, 4-(phenylmethyl)-3-pyridazinyl

HRID 916605Notes

Reaction equation

HRID 916605 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[N:26]=[N:27][CH:28]=[CH:29][C:30]=1[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=O)C.C[O-].[Na+]>CO>[CH2:31]([C:30]1[CH:29]=[CH:28][N:27]=[N:26][C:25]=1[O:24][C@@H:6]1[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 69421754HCID 69421754, compound

Product 1

HCID 69423484β-D-Glucopyranoside, 4-(phenylmethyl)-3-pyridazinylYield 86.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyloxy)-4-benzylpyridazine (0.055 g) in methanol (2 mL) was added sodium methoxide (28% solution in methanol, 0.010 mL), and the mixture was stirred for 30 minutes at room temperature. After the reaction mixture was concentrated under reduced pressure, the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=7/1) to give 4-benzyl-3-(β-D-Glucopyranosyloxy)pyridazine (0.032 g).

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=7/1)

Sources & evidence

ORD record
ord-3b03d0458553401184f7ebf878613fda
Source dataset
uspto-grants-2007_09
Patent number
US07271153B2

Reaction notes

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