Methanol → 3-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose

HRID 1689658Notes

Reaction equation

HRID 1689658 reaction equation
[CH3:1][C:2]1([CH3:18])[O:6][C@@H:5]([C@H:7]2[O:11][C@@H:10]3[O:12][C:13]([CH3:16])([CH3:15])[O:14][C@@H:9]3[C@@H:8]2[OH:17])[CH2:4][O:3]1.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CO>CN(C)C=O>[CH3:1][C:2]1([CH3:18])[O:6][CH:5]([CH:7]2[O:11][CH:10]3[O:12][C:13]([CH3:16])([CH3:15])[O:14][CH:9]3[CH:8]2[O:17][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 71570541,2:5,6-Bis-O-(1-methylethylidene)-alpha-D-allofuranose

Product 1

HCID 979073-O-Benzyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranoseYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,2:5,6-Di-O-isopropylidene-α-D-allofuranose (30A) (obtained from Pfanstiehl Laboratories Inc.) (40 g) in dimethylformamide at 0° C. was added sodium hydride in smaller portions. The reaction mixture was stirred for 1 h, benzyl bromide was added drop wise over a period of 1 h. The reaction mixture was stirred at room temperature for 16 h. Methanol was added to quench the reaction and dimethylformamide was removed under pressure. The syrup was extracted with ethyl acetate and washed with brine. Evaporation of the ethyl acetate layer yielded a semisolid (93%). Homogeneous by TLC.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 h
  2. customto quench
  3. customthe reaction and dimethylformamide
  4. customwas removed under pressure
  5. extractionThe syrup was extracted with ethyl acetate
  6. washwashed with brine
  7. customEvaporation of the ethyl acetate layer

Sources & evidence

ORD record
ord-9fa8e4dcfdf84074b527abc98274ae32
Source dataset
uspto-grants-2012_04
Patent number
US08153365B2

Reaction notes

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