Methyl iodide → HCID 66669406, compound

HRID 2106138Notes

Reaction equation

HRID 2106138 reaction equation
[C:1]1([C:7]([O:9][C@H:10]2[CH2:20][O:19][C@H:12]3[C@H:13]([OH:18])[C@H:14]([O:17][C@@H:11]23)[O:15][CH3:16])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21]I>CN(C=O)C.C(OCC)(=O)C.[Ag-]=O>[CH3:21][O:18][C@H:13]1[C@@H:12]2[O:19][CH2:20][C@H:10]([O:9][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:8])[C@@H:11]2[O:17][C@@H:14]1[O:15][CH3:16]

Participants

6

Reactant 2

HCID 6328Methyl iodideHCID 66669425HCID 66669425, compound

Product 1

HCID 66669406HCID 66669406, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 178418778HCID 178418778, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 3,6-anhydro-5-O-(phenylcarbonyl)-β-L-glucofuranoside (1.03 g, 3.7 mmol), silver (I) oxide (0.85 g, 3.7 mmol) and methyl iodide (0.34 mL, 5.5 mmol) in DMF (2 mL) was heated at 60° C. for 1 hour. After cooling to room temperature the reaction mixture was diluted with ethyl acetate (50 mL), filtered over celite, adsorbed on silica gel (10 g) and purified by flash chromatography (silica gel, 5-30% ethyl acetate-hexane) to give methyl 3,6-anhydro-2-O-methyl-5-O-(phenylcarbonyl)-β-L-glucofuranoside as a colorless oil, 0.82 g, 76% yield. 1H NMR (400 MHz; CDCl3): 8.11-8.09 (d, 2H), 7.60-7.56 (m, 1H), 7.46-7.44 (m, 2H), 5.24-5.20 (m, 1H), 5.18-5.09 (tr, 1H), 4.99 (s, 1H), 4.61-4.60 (d, 1H), 4.21-4.17 (tr, 1H), 4.08-4.03 (tr, 1H), 3.81 (s, 1H), 3.40 (s, 3H), 3.57 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. filtrationfiltered over celite
  3. custompurified by flash chromatography (silica gel, 5-30% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-637413b24a8a461898bd7f79a7e6ff53
Source dataset
uspto-grants-2009_08
Patent number
US07579473B2

Reaction notes

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