(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → HCID 131727790, compound

HRID 1863834Notes

Reaction equation

HRID 1863834 reaction equation
[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[C@@H:13]12[C:22](=[O:23])[O:21][C:19](=[O:20])[C@@H:14]1[CH2:15][CH2:16][CH2:17][CH2:18]2>CN(C1C=CN=CC=1)C.C1COCC1>[C:22]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[C:19]([OH:1])=[O:20])([OH:21])=[O:23].[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4]

Participants

5

Reactant 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 641660Hexahydrophthalic anhydride, cis-

Product 1

HCID 131727790HCID 131727790, compoundYield 806.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 20.0 g of D-glucose, 3.4 g of 4-(N,N-dimethylamino)pyridine, 68.0 g of TEA and 440 g of THF, a solution of 86.0 g of cis-1,2-cyclohexanedicarboxylic anhydride and 88 g of THF was added with stirring at room temperature, then the added mixture was stirred for 3 days. After the stirring, the solvent was removed from the resulting mixture under reduced pressure. To the concentrate, 600 g of chloroform and 300 g of ion-exchanged water was added, and was neutralized with hydrochloric acid. The neutralized organic layer was separated, washed with ion-exchanged water, and dried with anhydrous magnesium sulfate. Then the solvent was removed from the dried organic layer to obtain 160.1 g of crude pentakis-D-glucose (2-carboxycyclohexyl)carboxylate (abbreviated to “GLUCHA”).

Workup

  1. stirringthe added mixture was stirred for 3 days
  2. customAfter the stirring, the solvent was removed from the resulting mixture under reduced pressure
  3. additionTo the concentrate, 600 g of chloroform and 300 g of ion-exchanged water was added
  4. customThe neutralized organic layer was separated
  5. washwashed with ion-exchanged water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThen the solvent was removed from the dried organic layer

Sources & evidence

ORD record
ord-0a7dc2b3127142469256df401a798b88
Source dataset
uspto-grants-2009_12
Patent number
US07625689B2

Reaction notes

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