Reaktion #1951016

ord-0a7dc2b3127142469256df401a798b88

Reaktionsgleichung

O=C1OC(=O)[C@@H]2CCCC[C@H]12
cis-1,2-cyclohexanedicarboxylic anhydride
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
D-glucose
→
O=C(O)C1CCCCC1C(=O)O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
pentakis-D-glucose (2-carboxycyclohexyl)carboxylate

Edukte

O=C1OC(=O)[C@@H]2CCCC[C@H]12
cis-1,2-cyclohexanedicarboxylic anhydride
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
D-glucose
—
TEA

Reagenzien

CN(C)c1ccncc1
4-(N,N-dimethylamino)pyridine

Lösungsmittel

C1CCOC1
THF
C1CCOC1
THF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.STIRRINGthe added mixture was stirred for 3 days
  2. 2
    SonstigeAfter the stirring, the solvent was removed from the resulting mixture under reduced pressure
  3. 3
    workup.ADDITIONTo the concentrate, 600 g of chloroform and 300 g of ion-exchanged water was added
  4. 4
    SonstigeThe neutralized organic layer was separated
  5. 5
    Waschenwashed with ion-exchanged water
  6. 6
    Trocknendried with anhydrous magnesium sulfate
  7. 7
    SonstigeThen the solvent was removed from the dried organic layer

Vorschrift

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”).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07625689B2uspto-grants-2009_12