Reaction #1951016

ord-0a7dc2b3127142469256df401a798b88

Reaction equation

cis-1,2-cyclohexanedicarboxylic anhydride

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

Reactants

cis-1,2-cyclohexanedicarboxylic anhydride

D-glucose

—

TEA

Reagents

4-(N,N-dimethylamino)pyridine

Solvents

THF

Conditions

Detailed conditions

See reaction.notes.procedure_details.

Workup

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

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”).

Source

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