Reaction #56616

ord-2bbf9c81737847f3be6c5f6c91dd6089

Reaction equation

C=C(CO)C(CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC(=O)/C=C/c1ccc(O)c(O)c1
pubescenoside B
C=C(CO)C(CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC(=O)/C=C/c1ccc(O)c(O)c1
Compound 2
C=C(CO)C(CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC(=O)/C=C/c1ccc(O)c(O)c1
Pubescenoside B
→
O=C(O)/C=C/c1ccc(O)c(O)c1
caffeic acid
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
D-(+)-glucose

Reactants

—
compound 1
C=C(CO)C(CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC(=O)/C=C/c1ccc(O)c(O)c1
pubescenoside B
C=C(CO)C(CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC(=O)/C=C/c1ccc(O)c(O)c1
Compound 2
C=C(CO)C(CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)OC(=O)/C=C/c1ccc(O)c(O)c1
Pubescenoside B

Reagents

None

Solvents

O
H2O

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Acid hydrolysis of pubescenoside B: Compound 2 (15 mg) was hydrolyzed in a manner similar to that described for compound 1, yielding caffeic acid, D-(+)-glucose {[α]D21=+33.1° (c=0.1, H2O), determined after being dissolved in H2O for 24 hours} and compound 1a which was identified by comparing its 1H-NMR data with those described in the reference13.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07419960B2uspto-grants-2008_09