Ethanol → benzyl 2-deoxy-2-phthalimido-alpha-D-glucopyranoside

HRID 1707407Notes

Reaction equation

HRID 1707407 reaction equation
C([O:4][C@H:5]1[C@H:18]([O:19]C(=O)C)[C@@H:17]([CH2:23][O:24]C(=O)C)[O:16][C@@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@@H:6]1[N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38])(=O)C.C(OCC)(=O)C.C(O)C.CCCCCC>CO.C[O-].[Na+]>[C:29]1(=[O:38])[N:28]([C@@H:6]2[C@@H:5]([OH:4])[C@H:18]([OH:19])[C@@H:17]([CH2:23][OH:24])[O:16][C@@H:7]2[O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]12

Participants

7

Reactant 4

HCID 702EthanolHCID 8058HexaneHCID 8857Ethyl AcetateHCID 11237799(2R,3S,4R,5R,6R)-2-(Acetoxymethyl)-6-(benzyloxy)-5-(1,3-dioxoisoindolin-2-yl)tetrahydro-2H-pyran-3,4-diyl diacetate

Product 1

HCID 53964974benzyl 2-deoxy-2-phthalimido-alpha-D-glucopyranosideYield 89.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

Benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (3) (40.6 g, 84 mM) in 750 ml of dry methanol and 30 ml of 0.5M sodium methoxide was added to a 2 liter round bottomed flask equipped with magnetic stirring bar, saprum inlet and bent tube adapter and the contents stirred at room temperature for 18 hours. TLC indicated completion of the reaction. (The TLC solvent was 10:2:10 ethyl acetate: ethyl alcohol:hexane). To the mixture was added 15 g of Bio-Rad (Bio-Rad Laboratories, P.O. Box 708, 220Maple Ave., Rockville Center, N.Y. 11571) ion exchange resin AG-50W-X-8 (prewashed with H2O, methanol, and dried) and stirred for 5 minutes (pH should be ≤7.0). The mixture, after filtration followed by the removal of solvent, furnished benzyl 2-deoxy-2-phthalimido-α-D-glucopyranoside (1), 30 g (89.4% yield).

Workup

  1. customequipped with magnetic stirring bar, saprum inlet
  2. customcompletion of the reaction
  3. additionTo the mixture was added 15 g of Bio-Rad (Bio-Rad Laboratories, P.O. Box 708, 220Maple Ave., Rockville Center, N.Y. 11571) ion exchange resin
  4. dry with material(prewashed with H2O, methanol, and dried)
  5. stirringstirred for 5 minutes (pH should be ≤7.0)
  6. filtrationThe mixture, after filtration
  7. customfollowed by the removal of solvent

Sources & evidence

ORD record
ord-7e021bfe6c40443fa5fc098df0b1ba41
Source dataset
uspto-grants-1994_10
Patent number
US05352811

Reaction notes

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