HCID 131731391, compound → HCID 131731390, compound

HRID 1024326Notes

Reaction equation

HRID 1024326 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.[OH:13][C@H:14]1[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@H:17]([OH:18])[C@H:15]1[OH:16]>[OH-].[OH-].[Pd+2]>[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.[OH:13][C@@H:14]1[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@H:17]([OH:18])[C@H:15]1[OH:16]

Participants

3

Reactant 1

HCID 131731391HCID 131731391, compound

Product 1

HCID 131731390HCID 131731390, compound

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

Next, hydrogenation was carried out using a palladium hydroxide charcoal catalyst for deprotection of benzyl groups. Thus, a mixture of α-glucose gallate and β-glucose gallate was obtained. Palladium hydroxide was removed via Celite filtration. The obtained mixture was subjected to separation using 10% liquid B comprising eluent A (a 0.1% acetic acid aqueous solution) and eluent B (a 90% methanol aqueous solution) by fractionation HPLC (Develosil C30; 10×250 mm; Nomura Chemical) (for 40 minutes). Accordingly, 1-O-α-galloyl glucose and 1-O-β-galloyl glucose were separately obtained: Molecular MS [M+Na]+ m/z 354.9, α-1H NMR (400 MHz, CD3CD): δ 7.10 (2H, s, H-2, 6), 6.25 (1H, d, H-Glc1, J=3.66), 3.82-3.32 (5H, m, H-Glc), β-1H NMR (400 MHz, CD3CD): δ 7.10 (2H, s, H-2, 6), 5.63 (1H, d, H-Glc1, J=7.79), 3.84-3.32 (5H, m, H-Glc).

Sources & evidence

ORD record
ord-ef1479e259ba493f933b4820a1a8d755
Source dataset
uspto-grants-2014_05
Patent number
US08722868B2

Reaction notes

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