Pubescenoside B → (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

HRID 28338

Reaction equation

HRID 28338 reaction equation
C=C(C([O:19][C:20](/[CH:22]=[CH:23]/[C:24]1[CH:25]=[CH:26][C:27]([OH:31])=[C:28]([OH:30])[CH:29]=1)=[O:21])C[O:7][C@@H:8]1[O:13][C@H:12]([CH2:14][OH:15])[C@@H:11]([OH:16])[C@H:10]([OH:17])[C@H:9]1[OH:18])CO>O>[C:20]([OH:21])(=[O:19])/[CH:22]=[CH:23]/[C:24]1[CH:25]=[CH:26][C:27]([OH:31])=[C:28]([OH:30])[CH:29]=1.[O:7]=[CH:8][C@@H:9]([C@H:10]([C@@H:11]([C@@H:12]([CH2:14][OH:15])[OH:13])[OH:16])[OH:17])[OH:18]

Participants

4

Reactant 1

HCID 11464887Pubescenoside B2×

Product 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 689043Caffeic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Sources & evidence

ORD record
ord-2bbf9c81737847f3be6c5f6c91dd6089
Source dataset
uspto-grants-2008_09
Patent number
US07419960B2

Linked notes

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