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inquiryAbout Product Technical Details CAS: 58001-44-8 MF: C8H9NO5 MW: 199.16 EINECS: 261-069-2 Product Categories: antibiotic;Antibiotics Mol File: 58001-44-8.mol
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inquiryProduct Name Clavulanic acid CAS NO 58001-44-8 Apparence White Powder Purity 99%
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Clavulanic acid Basic information Product Name: Clavulanic acid Synonyms: (2r-(2-alpha,3z,5-alpha))-xo;3008-b;4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylicacid,
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factory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B
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Benzyl Clavulanate
clavulanic acid
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 0.75h; Ambient temperature; | 84% |
(2RS,5S)-<5-(3)H>Ornithine
B
clavulanic acid
Conditions | Yield |
---|---|
With cultures of Streptomyces clavuligerus (ATCC 27064) in a glycerol-based fermentation medium Product distribution; labelling studies also with incorporation (14)C, acid isolated as p-bromobenzyl ester; |
Conditions | Yield |
---|---|
With cultures of Streptomyces clavuligerus (ATCC 27064) in a glycerol-based fermentation medium Product distribution; labelling studies also with incorporation (14)C, acid isolated as p-bromobenzyl ester; |
clavulanic acid
Conditions | Yield |
---|---|
Streptomyces clavuligerus SC 2; |
Conditions | Yield |
---|---|
Streptomyces clavuligerus; examination of incorporation by labelled <5-(14)C, 5-(3)H>ornithine; |
methyl clavulanate
clavulanic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 70 percent / sodium hydroxide / H2O / 1.17 h / 0 °C 2: 69 percent / dimethylformamide / 1.5 h / Ambient temperature 3: 84 percent / H2 / palladium on carbon / ethanol / 0.75 h / 760 Torr / Ambient temperature View Scheme |
potassium clavulanate
clavulanic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 69 percent / dimethylformamide / 1.5 h / Ambient temperature 2: 84 percent / H2 / palladium on carbon / ethanol / 0.75 h / 760 Torr / Ambient temperature View Scheme |
clavulanic acid
Conditions | Yield |
---|---|
With NADPH at 26℃; pH=7.0; |
N,N-diisopropyl-1,2-ethanediamine
clavulanic acid
Conditions | Yield |
---|---|
In methanol; water; ethyl acetate for 0.25h; | 96% |
In ethyl acetate; isopropyl alcohol | 84% |
In methanol; ethyl acetate | 81% |
Conditions | Yield |
---|---|
In ethyl acetate | 83% |
In ethanol; ethyl acetate for 1h; | 68% |
In ethyl acetate; isopropyl alcohol | 67% |
1-Adamantanamine
clavulanic acid
(2R,5R)-3-[2-Hydroxy-eth-(Z)-ylidene]-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; compound with adamantan-1-ylamine
Conditions | Yield |
---|---|
In ethyl acetate | 81% |
In ethanol; ethyl acetate | 80% |
In methanol; ethyl acetate for 1h; | 76% |
In ethyl acetate; isopropyl alcohol | 76% |
Conditions | Yield |
---|---|
In ethyl acetate | 81% |
In ethyl acetate; isopropyl alcohol for 1h; | 77% |
In ethanol; ethyl acetate | 43% |
Stage #1: clavulanic acid With ammonium sulfate In water; ethyl acetate at 5℃; pH=1.30; Stage #2: tert-butylamine In methanol; ethyl acetate at 5℃; for 2h; pH-value; Concentration; |
tert-Octylamine
clavulanic acid
(2R,5R)-3-[2-Hydroxy-eth-(Z)-ylidene]-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; compound with 1,1,3,3-tetramethyl-butylamine
Conditions | Yield |
---|---|
In ethyl acetate | 80% |
In ethyl acetate; isopropyl alcohol for 1h; | 67% |
In ethanol; ethyl acetate | 35% |
clavulanic acid
methyl-4-aza-8-hydroxy-6-oxo-oct-2-enoate
Conditions | Yield |
---|---|
With methanol; diethylamine for 0.166667h; Ambient temperature; | 78% |
Conditions | Yield |
---|---|
In ethanol Ambient temperature; | 75% |
clavulanic acid
9-chloro-9-deoxyclavulanic acid
Conditions | Yield |
---|---|
With pyridine; methanesulfonyl chloride In acetonitrile at 25℃; for 24h; | 75% |
Conditions | Yield |
---|---|
With sodium hydroxide; dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane; ethyl acetate | 67% |
Conditions | Yield |
---|---|
In ethanol; ethyl acetate for 0.5h; | 61% |
Conditions | Yield |
---|---|
In tetrahydrofuran Ambient temperature; | 60% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In acetonitrile Ambient temperature; | 59% |
Conditions | Yield |
---|---|
In ethanol; ethyl acetate for 1h; | 54% |
In ethyl acetate; isopropyl alcohol | 31% |
In ethyl acetate | 3% |
Conditions | Yield |
---|---|
In ethanol; ethyl acetate for 1h; | 52.6% |
In ethyl acetate; isopropyl alcohol | 52% |
In ethyl acetate | 8% |
2-(2-Hydroxyethyl)pyridine
clavulanic acid
2-(2-pyridyl)ethyl clavulanate
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In acetonitrile Ambient temperature; | 50% |
N,N,N,N,-tetramethylethylenediamine
clavulanic acid
Conditions | Yield |
---|---|
In ethyl acetate; isopropyl alcohol for 1h; | 37% |
In ethyl acetate | 30% |
clavulanic acid
A
methyl (E)-3-(diethylamino)-2-propenoate
B
methyl 3-(2-hydroxyethyl)-pyrrole-4-carboxylate
C
methyl-4-aza-8-hydroxy-6-oxo-oct-2-enoate
Conditions | Yield |
---|---|
With diethylamine In methanol for 48h; Ambient temperature; | A 20% B 14% C 18% |
With Diethyl amine In methanol for 48h; Ambient temperature; | A 20% B 14% C 18% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In acetonitrile Ambient temperature; | 17% |
clavulanic acid
Conditions | Yield |
---|---|
With mercury(II) diacetate In 1,2-dimethoxyethane 1) r.t., 15 min, 2) 90-95 deg C (bath), 20 min; | A 5% B 5.5% |
clavulanic acid
(5R)-7-oxo-3-vinyl-4-oxa-1-azabicyclo[3.2.0]hept-2-ene
Conditions | Yield |
---|---|
With N,N-dimethyl-formamide dimethyl acetal In tetrahydrofuran | |
With N,N-dimethyl-formamide dimethyl acetal In tetrahydrofuran for 0.133333h; Ambient temperature; Yield given; | |
With N,N-dimethyl-formamide dimethyl acetal |
benzyl chloroformate
clavulanic acid
1-benzyloxycarbonylamino-4-hydroxybutan-2-one
Conditions | Yield |
---|---|
With hydrogenchloride; water; sodium hydrogencarbonate 1.) 2 h, 2.) water, THF, ice-cooling, 40 min; Yield given. Multistep reaction; |
3-chloro-benzenecarboperoxoic acid
clavulanic acid
(Z)-(3S,5R)-2-(2-hydroxyethylidene)-3-(m-chlorobenzoyloxy)clavam
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In 1,2-dimethoxyethane; dichloromethane 1.) 0 deg C, 3 h, 2.) room temperature, 15 h; | 60 mg |
methanol
clavulanic acid
A
methyl clavulanate
B
(Z)-(2R)-5-(2-hydroxyethylidene)-2-methoxycarbonylmethyl-2,5-dihydro-oxazole
C
(Z)-(3S,5R)-2-(2-hydroxyethylidene)-3-methoxyclavam
Conditions | Yield |
---|---|
With triethylamine at -30℃; for 0.833333h; electrolysis: platinum electrodes, I=200-250 mA; | A 5 mg B 75 mg C 10 mg |
With triethylamine at -30℃; for 0.833333h; electrolysis: platinum electrodes, current 200-250 mA; | A 5 mg B 75 mg C 10 mg |
methanol
clavulanic acid
A
methyl clavulanate
B
(Z)-(3S,5R)-2-(2-hydroxyethylidene)-3-methoxyclavam
C
(E)-(3S,5R)-3-acetoxy-2-formylmethyleneclavam
D
(Z)-(3S,5R)-3-acetoxy-2-formylmethyleneclavam
Conditions | Yield |
---|---|
With triethylamine at -30℃; for 0.833333h; Product distribution; electrolysis, platinum electrodes, current 200-250 mA; reactions of oxidative decarboxylation ( electrolysis, with Pb(OAc)4, decarboxylative rearrangement of diacyl peroxide) of clavulanic acid and its methyl ether; | A 5 mg B 10 mg C n/a D n/a |
lead(IV) tetraacetate
clavulanic acid
A
(Z)-(3S,5R)-3-acetoxy-2-(2-hydroxyethylidene)clavam
B
(Z)-(3S,5R)-3-acetoxy-2-(2-acetoxyethylidene)clavam
C
(E)-(3S,5R)-3-acetoxy-2-formylmethyleneclavam
D
(Z)-(3S,5R)-3-acetoxy-2-formylmethyleneclavam
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane; benzene at 70℃; for 0.333333h; | A 145 mg B 20 mg C n/a D n/a |
In 1,2-dimethoxyethane; benzene at 70℃; for 0.333333h; Yields of byproduct given; | A 145 mg B 20 mg C n/a D n/a |
In 1,2-dimethoxyethane; benzene at 70℃; for 0.333333h; Yield given. Title compound not separated from byproducts; | A 145 mg B 20 mg C n/a D n/a |
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