Sodium Methoxide → HCID 66765956, compound

HRID 556779Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([C@@H:20]2[O:46][C@H:45]([CH2:47][O:48]C(=O)C(C)(C)C)[C@@H:37]([O:38]C(=O)C(C)(C)C)[C@H:29]([O:30]C(=O)C(C)(C)C)[C@H:21]2[O:22]C(=O)C(C)(C)C)=[CH:5][C:6]2[C:10]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][O:8][C:7]=2[CH:19]=1.C[O-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:4]([C@@H:20]2[O:46][C@H:45]([CH2:47][OH:48])[C@@H:37]([OH:38])[C@H:29]([OH:30])[C@H:21]2[OH:22])=[CH:5][C:6]2[C:10]([CH2:11][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:9][O:8][C:7]=2[CH:19]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 1-[6-methoxy-3-(2-phenylethyl)-benzo[b]furan-5-yl]-1-deoxy-2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranose (0.03 g) in methanol (4 mL) was added sodium methoxide (28% methanol solution, 0.038 mL), and the mixture was stirred at 50° C. for 6 hours. The reaction mixture was purified directly by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1) to give the title compound (0.015 g).

Workup

customThe reaction mixture was purified directly by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1)

Sources & evidence

ORD record: ord-fad62bdd5e8b498b9f51649bcd99064e
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058245B2

Reaction notes

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