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89771-75-5

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Basic Information
CAS No.: 89771-75-5
Name: (3R,4S,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid
Article Data: 4
Molecular Structure:
Molecular Structure of 89771-75-5 ((3R,4S,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid)
Formula: C10H13O10P
Molecular Weight: 324.181
Synonyms: 5-enolpyruvylshikimate 3-phosphate;enolpyruvylshikimate 3-phosphate;5-enolpyruvoylshikimate-3-phosphate;5-(enolpyruvyl)shikimate-3-phosphate;(3R,4S,5R)-5-(1-Carboxy-vinyloxy)-4-hydroxy-3-phosphonooxy-cyclohex-1-enecarboxylic acid;5-enol pyruvyl shikimate 3-phosphate;5-enolpyruvylshikimate-3-phosphate;
Density: 1.75g/cm3
Boiling Point: 724°Cat760mmHg
Flash Point: 391.6°C
PSA: 180.63000
LogP: -0.77660
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phosphoenolpyruvic acid

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89771-75-5

5-enol-pyruvoylshikimate 3-phosphate (EPSP)

Conditions
ConditionsYield
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
ConditionsYield
With sodium hydroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene 1.) C5H5N, rt, 72h, 2.) 5h, 0 deg C; Multistep reaction;
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(3R-(3α,4α,5β))-O-3-phospho-O-5-(1S-1-carboxy-1-(phosphooxy)-ethyl)shikimic acid

A

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phosphoenolpyruvic acid

B

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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
ConditionsYield
With glycine at 25℃; pH=2.5 - 3.5; Product distribution; Kinetics; Further Variations:; pH-values; Reagents;
...Expand
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methyl 3,4-O-isopropylideneshikimate

89771-75-5

5-enol-pyruvoylshikimate 3-phosphate (EPSP)

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

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    89771-75-5

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