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

Base Information

Chemical Name:(3R,4S,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid
CAS No.:89771-75-5
Molecular Formula:C10H13O10P
Molecular Weight:324.181
Hs Code.:

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;

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

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

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Total 11 raw suppliers

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

Chemical Property:

Vapor Pressure:3.34E-24mmHg at 25°C
Boiling Point:724°Cat760mmHg
Flash Point:391.6°C
PSA：180.63000
Density:1.75g/cm³
LogP:-0.77660

Purity/Quality:: 99% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

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

There total 11 articles about (3R,4S,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

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

: 89771-75-5,27840-48-8
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

Guidance literature:: 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

With dmap; sodium hydroxide; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dirhodium tetraacetate; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; benzene;
DOI:10.1016/S0040-4039(00)98455-7

Reference yield:

: 96251-70-6
compound Z₁

: 89771-75-5,27840-48-8
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

Guidance literature:: 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

With dmap; sodium hydroxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)98455-7

Reference yield:

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

: 89771-75-5,27840-48-8
5-enol-pyruvoylshikimate 3-phosphate (EPSP)

Guidance literature:: 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

With dmap; sodium hydroxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; water;
DOI:10.1016/S0040-4039(00)98455-7