Methanol → HCID 69422867, compound

HRID 916581Notes

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[C:30]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][O:40][CH2:41]OC)=[CH:34][CH:33]=2)=[C:29]([CH3:44])[CH:28]=[C:27]([CH3:45])[N:26]=1)(=O)C.[OH-:46].[Na+].[CH3:48]O>>[C@@H:6]1([O:24][C:25]2[C:30]([CH2:31][C:32]3[CH:33]=[CH:34][C:35]([CH2:38][CH:39]([O:46][CH3:48])[O:40][CH3:41])=[CH:36][CH:37]=3)=[C:29]([CH3:44])[CH:28]=[C:27]([CH3:45])[N:26]=2)[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]

Participants

Reactant 3

HCID 887Methanol

HCID 14798Sodium Hydroxide

HCID 69422815HCID 69422815, compound

Product 1

HCID 69422867HCID 69422867, compound

Procedure

To a solution of 2-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyloxy)-3-[4-(2-methoxymethyloxyethyl)benzyl]-4,6-dimethylpyridine (0.13 g) in methanol (4.0 mL) was added 2 mol/L aqueous sodium hydroxide solution (0.50 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 preparative thin layer chromatography on silica gel (developing solvent: dichloromethane/methanol=9/1) to give 2-(β-D-glucopyranosyloxy)-3-[4-(2-methoxy-methyloxyethyl)benzyl]-4,6-dimethylpyridine (0.086 g).

Workup

concentrationAfter the reaction mixture was concentrated under reduced pressure
customthe residue was purified by preparative thin layer chromatography on silica gel (developing solvent: dichloromethane/methanol=9/1)

Sources & evidence

ORD record: ord-51b5aa4165eb48c89546cc9744ecb9a6
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271153B2

Reaction notes

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