beta-Maltose → HCID 86748941, compound

HRID 1757381Notes

Reaction equation

HRID 1757381 reaction equation
[NH2:1][CH2:2][CH:3]([OH:22])[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[CH2:23]([OH:45])[C@H:24]1[O:29][C@H:28]([O:30][C@H:31]2[C@H:36]([OH:37])[C@@H:35]([OH:38])[C@H:34]([OH:39])[O:33][C@@H:32]2[CH2:40]O)[C@H:27]([OH:42])[C@@H:26]([OH:43])[C@@H:25]1[OH:44]>[Pd].CO>[CH2:6]([O:5][CH2:4][CH:3]([OH:22])[CH2:2][N:1]([C:6](=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:40][C@@H:32]([C@H:31]([C@@H:36]([C@@H:35]([CH2:34][OH:39])[OH:38])[OH:37])[O:30][C@H:28]1[O:29][C@H:24]([CH2:23][OH:45])[C@@H:25]([OH:44])[C@H:26]([OH:43])[C@H:27]1[OH:42])[OH:33])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 2

HCID 6255beta-MaltoseHCID 10358347HCID 10358347, compound

Product 1

HCID 86748941HCID 86748941, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 1-liter eggplant type flask equipped with a reflux condenser was charged with 22.7 g (72 mmol) of 1-amino-3-hexadecyloxy-2-propanol, 23.5 g (69 mmol) of maltose and 350 g of methanol. After stirring the mixture for 20 hours at room temperature under a nitrogen atmosphere, it was heated and stirred at 80° C. for 1 hour. The thus-obtained solution was transferred to a 970-ml autoclave, and 2.26 g of palladium on carbon was added, thereby subjecting the solution to hydrogenolysis at 50° C. for 16 hours under a hydrogen pressure of 100 kg/cm2. The catalyst was removed by filtering the hot mixture, and the filtrate was allowed to cool to form crystals. The crystals were recrystallized again from methanol, thereby obtaining 15.2 g (yield: 33%) of the title compound (2Be) as a colorless solid.

Workup

  1. customA 1-liter eggplant type flask equipped with a reflux condenser
  2. temperatureit was heated
  3. stirringstirred at 80° C. for 1 hour
  4. additionwas added
  5. customat 50° C.
  6. customfor 16 hours
  7. customThe catalyst was removed
  8. filtrationby filtering the hot mixture
  9. temperatureto cool
  10. customto form crystals
  11. customThe crystals were recrystallized again from methanol

Sources & evidence

ORD record
ord-ea75e4afca1043d490f1c65e7bf089f7
Source dataset
uspto-grants-1995_08
Patent number
US05446027

Reaction notes

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