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2,3,4,6-tetra-O-benzyl-1-(3’,4’,5’-tri-O-benzylgalloyl)-β-D-glucopyranose
β-glucogallin
Conditions | Yield |
---|---|
With 20% palladium hydroxide-activated charcoal; hydrogen In tetrahydrofuran at 20 - 25℃; for 12h; | 96% |
With palladium 10% on activated carbon; hydrogen In methanol; ethyl acetate under 2585.81 Torr; for 5h; Inert atmosphere; | 95% |
L-Cysteine methyl ester
furosin
A
(R)-1,2,6-Trihydroxy-4,11-dioxo-4,8,9,11-tetrahydro-7H-5,12-dioxa-10-thia-7-aza-benzo[def]chrysene-8-carboxylic acid methyl ester
B
β-glucogallin
Conditions | Yield |
---|---|
With ammonium formate In water; acetonitrile at 80℃; | A 60% B 74% |
furosin
A
(R)-1,2,6-Trihydroxy-4,11-dioxo-4,8,9,11-tetrahydro-7H-5,12-dioxa-10-thia-7-aza-benzo[def]chrysene-8-carboxylic acid methyl ester
B
β-glucogallin
Conditions | Yield |
---|---|
With L-Cysteine methyl ester; ammonium formate In water; acetonitrile at 80℃; | A 60% B 74% |
1-galloyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose
β-glucogallin
Conditions | Yield |
---|---|
With methanol; sodium methylate |
3,4,5-trihydroxybenzoic acid
B
β-glucogallin
Conditions | Yield |
---|---|
In water for 96h; | A 190 mg B 230 mg |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0.17 h / 20 °C / Inert atmosphere; Molecular sieve 1.2: 3.33 h / Inert atmosphere; Molecular sieve 2.1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 5 h / 2585.81 Torr / Inert atmosphere View Scheme |
β-glucogallin
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 2585.81 Torr; for 4h; | |
With 10 wt% Pd(OH)2 on carbon; hydrogen In ethanol; acetone at 20℃; for 4h; |
3,4,5-trihydroxybenzoic acid
β-glucogallin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 80 °C / Inert atmosphere 2: thionyl chloride / dichloromethane 3: dichloromethane / 72 h / Inert atmosphere 4: perchloric acid; silica gel / acetonitrile / 24 h 5: hydrogen; palladium 10% on activated carbon / ethanol / 4 h / 20 °C / 2585.81 Torr View Scheme |
3,4,5-tribenzyloxybenzoic acid
β-glucogallin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: thionyl chloride / dichloromethane 2: dichloromethane / 72 h / Inert atmosphere 3: perchloric acid; silica gel / acetonitrile / 24 h 4: hydrogen; palladium 10% on activated carbon / ethanol / 4 h / 20 °C / 2585.81 Torr View Scheme |
3,4,5-tris(benzyloxy)benzoyl chloride
β-glucogallin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: dichloromethane / 72 h / Inert atmosphere 2: perchloric acid; silica gel / acetonitrile / 24 h 3: hydrogen; palladium 10% on activated carbon / ethanol / 4 h / 20 °C / 2585.81 Torr View Scheme | |
Multi-step reaction with 2 steps 1: N,N,N,N,-tetramethylethylenediamine / dichloromethane / 48 h / Reflux 2: hydrogen; 20% palladium hydroxide-activated charcoal / tetrahydrofuran / 12 h / 20 - 25 °C View Scheme |
1-O-(3,4,5-tris(benzyloxy)benzoyl)-4,6-O-benzylidene-β-D-glucopyranose
β-glucogallin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: perchloric acid; silica gel / acetonitrile / 24 h 2: hydrogen; palladium 10% on activated carbon / ethanol / 4 h / 20 °C / 2585.81 Torr View Scheme |
Conditions | Yield |
---|---|
With recombinant Quercus robur UGT84A13 In glycerol at 30℃; pH=6; Kinetics; Enzymatic reaction; | |
With Punica granatum UDP-glucosyltransferase 84A23; 2-hydroxyethanethiol In aq. buffer at 30℃; for 1h; pH=7; Enzymatic reaction; |
2,3,4,6-Tetra-O-benzyl-D-glucopyranose
β-glucogallin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N,N,N,N,-tetramethylethylenediamine / dichloromethane / 48 h / Reflux 2: hydrogen; 20% palladium hydroxide-activated charcoal / tetrahydrofuran / 12 h / 20 - 25 °C View Scheme |
Heptabenzyl-α-D-glucogallin
A
β-glucogallin
B
1-O-galloyl-α-D-glucopyranose
Conditions | Yield |
---|---|
With 10 wt% Pd(OH)2 on carbon; hydrogen In methanol |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 1 h / 20 °C / Inert atmosphere 2: 10 wt% Pd(OH)2 on carbon; hydrogen / acetone; ethanol / 4 h / 20 °C View Scheme |
1,6-di-O-galloyl-(α/β)-glucopyranose
β-glucogallin
A
3,4,5-trihydroxybenzoic acid
B
6-O-galloyl-D-glucopyranose
C
1,2,6-tri-O-galloyl β-D-glucopyranoside
Conditions | Yield |
---|---|
In water at 40℃; for 5h; 2-O-galloyltransferase, citrate buffer, pH 5.0; Yield given; |
β-glucogallin
A
4-O-digalloyl-1,2,3,6-tetra-O-galloyl-β-D-glucose
B
2-O-digalloyl-1,3,4,6-tetra-O-galloyl-β-D-glucose
Conditions | Yield |
---|---|
With citrate buffer; galloyltransferase (EC 2.3.1.-) In water at 30℃; for 2h; pH=4; Enzyme kinetics; Acylation; |
4-O-digalloyl-1,2,3,6-tetra-O-galloyl-β-D-glucose
β-glucogallin
Conditions | Yield |
---|---|
With citrate buffer; galloyltransferase (EC 2.3.1.-) In water at 30℃; for 2h; pH=4; Enzyme kinetics; Acylation; |
2-O-digalloyl-1,3,4,6-tetra-O-galloyl-β-D-glucose
β-glucogallin
A
C55H40O34
B
C55H40O34
Conditions | Yield |
---|---|
With citrate buffer; galloyltransferase (EC 2.3.1.-) In water at 30℃; for 2h; pH=4; Enzyme kinetics; Acylation; |
Conditions | Yield |
---|---|
With citrate buffer; galloyltransferase (EC 2.3.1.-) In water at 30℃; for 2h; pH=4; Enzyme kinetics; Acylation; |
β-glucogallin
Conditions | Yield |
---|---|
In aq. buffer at 22℃; pH=10; Kinetics; pH-value; Time; |
cyanidin-3-glucoside
β-glucogallin
3,5-di-O-β-D-glucopyranoside of cyanidin
Conditions | Yield |
---|---|
With citric acid at 30℃; for 0.25h; pH=5.6; Catalytic behavior; Enzymatic reaction; |
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