CAS No.89771-75-5,(3R,4S,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid Suppliers

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1-cyclohexene-1-carboxylic acid, 5-[(1-carboxyethenyl)oxy]-4-hydroxy-3-(phosphonooxy)-, (3R,4S,5R)-

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Zibo Hangyu Biotechnology Development Co., Ltd

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(3R,4S,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid

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1-cyclohexene-1-carboxylic acid, 5-[(1-carboxyethenyl)oxy]-4-hydroxy-3-(phosphonooxy)-, (3R,4S,5R)-

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1-cyclohexene-1-carboxylic acid, 5-[(1-carboxyethenyl)oxy]-4-hydroxy-3-(phosphonooxy)-, (3R,4S,5R)-

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(3R,4S,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid

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Shanghai Chinqesen Biotechnology Co., Ltd.

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ZHEJIANG JIUZHOU CHEM CO.,LTD

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(3R,4S,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid

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Jiangsu Jiumu Biological Technology Co., Ltd.(Lianyungang Bright-Sea Pharmaceutical Technology Co., Ltd.)

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(3R,4S,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid

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Synthetic route

: 138-08-9
phosphoenolpyruvic acid

: 63959-45-5
shikimate 3-phosphate (S3P)

: 89771-75-5
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

Conditions

Conditions	Yield
5-enol-pyruvoylshikimate 3-phosphate (EPSPS);
With ammonium heptamolybdate; EcaroA-T42M enolpyruvylshikimate 3-phosphate synthase; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid at 30℃; pH=7.0; Enzyme kinetics; Further Variations:; Reagents;

: 96251-72-8
(4aR,8R,8aS)-8-{Bis-[2-(4-nitro-phenyl)-ethoxy]-phosphoryloxy}-3-methylene-2-oxo-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester

: 89771-75-5
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

Conditions

Conditions	Yield
With sodium hydroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene 1.) C5H5N, rt, 72h, 2.) 5h, 0 deg C; Multistep reaction;

: 625091-49-8
(3R-(3α,4α,5β))-O-3-phospho-O-5-(1S-1-carboxy-1-(phosphooxy)-ethyl)shikimic acid

A: 138-08-9
phosphoenolpyruvic acid

B: 138-59-0
shikimic acid

C: 89771-75-5
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

D: (3aR,7R,7aS)-2-Methyl-7-phosphonooxy-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-2,5-dicarboxylic acid

Conditions

Conditions	Yield
With glycine at 25℃; pH=2.5 - 3.5; Product distribution; Kinetics; Further Variations:; pH-values; Reagents;

...Expand

: 88165-26-8
methyl 3,4-O-isopropylideneshikimate

: 89771-75-5
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 85 percent / Rh2(OAc)4 / benzene / Heating 2: Et3N / CH2Cl2 3: CH2Cl2 / Ambient temperature 4: 83 percent / dimethylsulfoxide / 6 h / 95 °C 5: 90 percent / 80percent aqueous acetic acid / 3 h / 65 - 70 °C 6: NaOH / tetrahydrofuran; H2O / 3 h / 0 °C 7: water-soluble carbodiimide, DMAP / tetrahydrofuran / 3 h / Ambient temperature 9: 1.) diazabicyclo<5.4.0>undec-7-ene, 2.) aqueous NaOH / 1.) C5H5N, rt, 72h, 2.) 5h, 0 deg C View Scheme

Yield

Multi-step reaction with 9 steps
1: 85 percent / Rh2(OAc)4 / benzene / Heating
2: Et3N / CH2Cl2
3: CH2Cl2 / Ambient temperature
4: 83 percent / dimethylsulfoxide / 6 h / 95 °C
5: 90 percent / 80percent aqueous acetic acid / 3 h / 65 - 70 °C
6: NaOH / tetrahydrofuran; H2O / 3 h / 0 °C
7: water-soluble carbodiimide, DMAP / tetrahydrofuran / 3 h / Ambient temperature
9: 1.) diazabicyclo<5.4.0>undec-7-ene, 2.) aqueous NaOH / 1.) C5H5N, rt, 72h, 2.) 5h, 0 deg C
View Scheme

: 96251-71-7
methyl <(4aR),4aβ,8α,8aα>-2,3,4a,5,8,8a-hexahydro-2-oxo-3-methylene-8-hydroxy-1,4-benzodioxin-6-carboxylate

: 89771-75-5
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 1.) diazabicyclo<5.4.0>undec-7-ene, 2.) aqueous NaOH / 1.) C5H5N, rt, 72h, 2.) 5h, 0 deg C View Scheme

: 96251-70-6
compound Z1

: 89771-75-5
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: water-soluble carbodiimide, DMAP / tetrahydrofuran / 3 h / Ambient temperature 3: 1.) diazabicyclo<5.4.0>undec-7-ene, 2.) aqueous NaOH / 1.) C5H5N, rt, 72h, 2.) 5h, 0 deg C View Scheme

: 96251-69-3
(3R,4R,5R)-3,4-Dihydroxy-5-(1-methoxycarbonyl-vinyloxy)-cyclohex-1-enecarboxylic acid methyl ester

: 89771-75-5
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: NaOH / tetrahydrofuran; H2O / 3 h / 0 °C 2: water-soluble carbodiimide, DMAP / tetrahydrofuran / 3 h / Ambient temperature 4: 1.) diazabicyclo<5.4.0>undec-7-ene, 2.) aqueous NaOH / 1.) C5H5N, rt, 72h, 2.) 5h, 0 deg C View Scheme

: 99655-79-5
methyl <(1R),1α,5β,6α>-5-<<1-(methoxycarbonyl)ethenyl>oxy>-8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-2-ene-3-carboxylate

: 89771-75-5
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 90 percent / 80percent aqueous acetic acid / 3 h / 65 - 70 °C 2: NaOH / tetrahydrofuran; H2O / 3 h / 0 °C 3: water-soluble carbodiimide, DMAP / tetrahydrofuran / 3 h / Ambient temperature 5: 1.) diazabicyclo<5.4.0>undec-7-ene, 2.) aqueous NaOH / 1.) C5H5N, rt, 72h, 2.) 5h, 0 deg C View Scheme

: 96283-92-0
methyl <(1R),1α,5β,6α>-5--8,8-dimethyl-7,9-dioxabicyclo<4.3.0>non-2-ene-3-carboxylate

: 89771-75-5
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: Et3N / CH2Cl2 2: CH2Cl2 / Ambient temperature 3: 83 percent / dimethylsulfoxide / 6 h / 95 °C 4: 90 percent / 80percent aqueous acetic acid / 3 h / 65 - 70 °C 5: NaOH / tetrahydrofuran; H2O / 3 h / 0 °C 6: water-soluble carbodiimide, DMAP / tetrahydrofuran / 3 h / Ambient temperature 8: 1.) diazabicyclo<5.4.0>undec-7-ene, 2.) aqueous NaOH / 1.) C5H5N, rt, 72h, 2.) 5h, 0 deg C View Scheme

Yield

Multi-step reaction with 8 steps
1: Et3N / CH2Cl2
2: CH2Cl2 / Ambient temperature
3: 83 percent / dimethylsulfoxide / 6 h / 95 °C
4: 90 percent / 80percent aqueous acetic acid / 3 h / 65 - 70 °C
5: NaOH / tetrahydrofuran; H2O / 3 h / 0 °C
6: water-soluble carbodiimide, DMAP / tetrahydrofuran / 3 h / Ambient temperature
8: 1.) diazabicyclo<5.4.0>undec-7-ene, 2.) aqueous NaOH / 1.) C5H5N, rt, 72h, 2.) 5h, 0 deg C
View Scheme

: 96251-67-1
2-Dimethylaminomethyl-2-((3aS,4R,7aR)-6-methoxycarbonyl-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yloxy)-malonic acid dimethyl ester

: 89771-75-5
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: CH2Cl2 / Ambient temperature 2: 83 percent / dimethylsulfoxide / 6 h / 95 °C 3: 90 percent / 80percent aqueous acetic acid / 3 h / 65 - 70 °C 4: NaOH / tetrahydrofuran; H2O / 3 h / 0 °C 5: water-soluble carbodiimide, DMAP / tetrahydrofuran / 3 h / Ambient temperature 7: 1.) diazabicyclo<5.4.0>undec-7-ene, 2.) aqueous NaOH / 1.) C5H5N, rt, 72h, 2.) 5h, 0 deg C View Scheme

Yield

Multi-step reaction with 7 steps
1: CH2Cl2 / Ambient temperature
2: 83 percent / dimethylsulfoxide / 6 h / 95 °C
3: 90 percent / 80percent aqueous acetic acid / 3 h / 65 - 70 °C
4: NaOH / tetrahydrofuran; H2O / 3 h / 0 °C
5: water-soluble carbodiimide, DMAP / tetrahydrofuran / 3 h / Ambient temperature
7: 1.) diazabicyclo<5.4.0>undec-7-ene, 2.) aqueous NaOH / 1.) C5H5N, rt, 72h, 2.) 5h, 0 deg C
View Scheme

: 96283-93-1
[2,2-Bis-methoxycarbonyl-2-((3aS,4R,7aR)-6-methoxycarbonyl-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yloxy)-ethyl]-trimethyl-ammonium; iodide

: 89771-75-5
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 83 percent / dimethylsulfoxide / 6 h / 95 °C 2: 90 percent / 80percent aqueous acetic acid / 3 h / 65 - 70 °C 3: NaOH / tetrahydrofuran; H2O / 3 h / 0 °C 4: water-soluble carbodiimide, DMAP / tetrahydrofuran / 3 h / Ambient temperature 6: 1.) diazabicyclo<5.4.0>undec-7-ene, 2.) aqueous NaOH / 1.) C5H5N, rt, 72h, 2.) 5h, 0 deg C View Scheme

: 89771-75-5
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

: 617-12-9
chorismic acid

Conditions

Conditions	Yield
Neurospora crassa chorismate synthase;
With 2-[Bis(2-hydroxyethyl)imino]-2-(hydroxymethyl)-1,3-propanediol Hydrochloride; potassium chloride; Flavin mononucleotide; NADPH; magnesium chloride at 25℃; Neurospora crassa chorismate synthase, pH 7.0; isotope effect;
With sodium dithionite; 17 μM chorsmate synthase; 20μM reduced flavin cofactor (FMNH2) In water at 25℃; Rate constant; Mechanism; detection of modified flavin mononucleotide (FMN) intermediate during the catalytic cycle;
With sodium dithionite; recombinant Escherichia coli chorismate synthase; reduced FMN In various solvent(s) at 25℃; pH=7.5; Kinetics; Further Variations:; Reagents;

: 89771-75-5
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

A: 63959-45-5
shikimate 3-phosphate (S3P)

B: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With perchloric acid at 25℃; Rate constant;

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