Sodium Methoxide → HCID 69422406, compound

HRID 916604Notes

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[CH:26]=[N:27][CH:28]=[CH:29][C:30]=1[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][O:40]C(=O)C2C=CC=CC=2)=[CH:34][CH:33]=1)(=O)C.C[O-].[Na+]>CO>[C@@H:6]1([O:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][C:30]=2[CH2:31][C:32]2[CH:33]=[CH:34][C:35]([CH2:38][CH2:39][OH:40])=[CH:36][CH:37]=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

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyloxy)-4-[4-(2-benzoyloxyethyl)benzyl]pyridine (0.086 g) in methanol (1 mL) was added sodium methoxide (28% solution in methanol, 0.008 mL), and the mixture was stirred for 23 hours at 25° C. After the reaction mixture was concentrated under reduced pressure, the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=4/1) to give 3-(β-D-glucopyranosyloxy)-4-[4-(2-hydroxy-ethyl)benzyl]pyridine (0.044 g).

Workup

concentrationAfter the reaction mixture was concentrated under reduced pressure
customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=4/1)

Sources & evidence

ORD record: ord-c070de6fc6f0483c9a006f941a03a626
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271153B2

Reaction notes

Loading…