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

Base Information

Chemical Name:(3R-(3α,4α,5β))-O-3-phospho-O-5-(1S-1-carboxy-1-(phosphooxy)-ethyl)shikimic acid
CAS No.:625091-49-8
Molecular Formula:C₁₀H₁₆O₁₄P₂
Molecular Weight:422.176
Hs Code.:

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

Suppliers and Price of (3R-(3α,4α,5β))-O-3-phospho-O-5-(1S-1-carboxy-1-(phosphooxy)-ethyl)shikimic acid

Supply Marketing:

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

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (3R-(3α,4α,5β))-O-3-phospho-O-5-(1S-1-carboxy-1-(phosphooxy)-ethyl)shikimic acid

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (3R-(3α,4α,5β))-O-3-phospho-O-5-(1S-1-carboxy-1-(phosphooxy)-ethyl)shikimic acid

There total 8 articles about (3R-(3α,4α,5β))-O-3-phospho-O-5-(1S-1-carboxy-1-(phosphooxy)-ethyl)shikimic 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:

: (3R-(3α,4α,5β))-O-3-phospho-O-5-(1R-1-carboxy-1-(phosphooxy)-2,2-dibromoethyl)shikimate hexasodium salt

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

: (S)-4-((1R,5R,6S)-3-Carboxy-6-hydroxy-5-phosphonooxy-cyclohex-3-enyloxy)-2-hydroxy-2-oxo-2λ⁵-[1,3,2]dioxaphospholane-4-carboxylic acid

Guidance literature:: (3R-(3α,4α,5β))-O-3-phospho-O-5-(1R-1-carboxy-1-(phosphooxy)-2,2-dibromoethyl)shikimate hexasodium salt; With cetyltrimethylammonim bromide; In methanol; water; at 20 ℃;

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; diisopropylamine; In methanol; water; for 0.666667h; Title compound not separated from byproducts; UV-irradiation;
DOI:10.1021/ja036627+

Reference yield:

: (3aR,7R,7aS)-7-(2,2-Dibromo-1-hydroxy-1-methoxycarbonyl-ethoxy)-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

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

Guidance literature:: Multi-step reaction with 10 steps

1.1: PCl₃; pyridine / CH₂Cl₂ / 0.5 h / -78 °C

2.1: pyridine / CH₂Cl₂ / 4 h / -78 °C

3.1: 928 mg / m-CPBA / CH₂Cl₂ / 17 h / -78 - 20 °C

4.1: aq. HCl; acetic acid / 36 h / 20 °C

4.2: 26 percent / silica gel / hexane; ethyl acetate / 15 h / 20 °C

5.1: 66 percent / K₂CO₃; silica gel; Ms 4Ae / acetonitrile / 17 h / 20 °C

6.1: tetrazole / tetrahydrofuran / 4.5 h / 20 °C

7.1: 365 mg / m-CPBA / tetrahydrofuran; CH₂Cl₂ / 1 h

8.1: DBU / acetonitrile / 4.5 h / 20 °C

9.1: aq. NaOH / 2 h / 20 °C

10.1: cetyltrimethylammonium bromide / H₂O; methanol / 20 °C

10.2: diisopropylamine; AIBN; n-Bu₃SnH / methanol; H₂O / 0.67 h / UV-irradiation

With pyridine; 1H-tetrazole; hydrogenchloride; sodium hydroxide; cetyltrimethylammonim bromide; silica gel; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; phosphorus trichloride; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/ja036627+

Reference yield:

: C₁₅H₁₉Br₂Cl₂O₈P

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

Guidance literature:: Multi-step reaction with 9 steps

1.1: pyridine / CH₂Cl₂ / 4 h / -78 °C

2.1: 928 mg / m-CPBA / CH₂Cl₂ / 17 h / -78 - 20 °C

3.1: aq. HCl; acetic acid / 36 h / 20 °C

3.2: 26 percent / silica gel / hexane; ethyl acetate / 15 h / 20 °C

4.1: 66 percent / K₂CO₃; silica gel; Ms 4Ae / acetonitrile / 17 h / 20 °C

5.1: tetrazole / tetrahydrofuran / 4.5 h / 20 °C

6.1: 365 mg / m-CPBA / tetrahydrofuran; CH₂Cl₂ / 1 h

7.1: DBU / acetonitrile / 4.5 h / 20 °C

8.1: aq. NaOH / 2 h / 20 °C

9.1: cetyltrimethylammonium bromide / H₂O; methanol / 20 °C

9.2: diisopropylamine; AIBN; n-Bu₃SnH / methanol; H₂O / 0.67 h / UV-irradiation

With pyridine; 1H-tetrazole; hydrogenchloride; sodium hydroxide; cetyltrimethylammonim bromide; silica gel; potassium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/ja036627+