Methyl 4,5-O-diacetyl-(-)-shikimate 3-phosphate

Base Information

• Chemical Name: Methyl 4,5-O-diacetyl-(-)-shikimate 3-phosphate
• CAS No.: 1053643-69-8
• Molecular Formula: C₁₂H₁₇O₁₀P
• Molecular Weight: 352.235
• Mol file: 1053643-69-8.mol

Synonyms:Methyl 4,5-O-diacetyl-(-)-shikimate 3-phosphate

Chemical Property of Methyl 4,5-O-diacetyl-(-)-shikimate 3-phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 4,5-O-diacetyl-(-)-shikimate 3-phosphate

There total 9 articles about Methyl 4,5-O-diacetyl-(-)-shikimate 3-phosphate 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: 80.0%

Methyl 4,5-O-diacetyl-(-)-shikimate dibenzyl 3-phosphate (143308-78-5) → Methyl 4,5-O-diacetyl-(-)-shikimate 3-phosphate (1053643-69-8)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jo00047a049

Reference yield:

shikimic acid (138-59-0) → Methyl 4,5-O-diacetyl-(-)-shikimate 3-phosphate (1053643-69-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / Amberlite IR 120 / 12 h / Heating

2: 96 percent / camphorsulfonic acid / 0.25 h / Ambient temperature

3: 100 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

4: 94 percent / aq. HOAc / tetrahydrofuran / 6 h / 70 °C

5: 1.) dibutyltin oxide / 1.) benzene, reflux, 1 h, 2.) DMF, 30 min

6: 100 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 50 °C

7: 89 percent / 80percent aq. HOAc / 0.25 h

8: tetrazole / CH₂Cl₂ / 2 h / Ambient temperature

9: 0.304 g / m-CPBA / CH₂Cl₂ / 2 h / -40 °C

10: 80 percent / bromotrimethylsilane / CH₂Cl₂ / 1 h / 0 °C

With 1H-tetrazole; dmap; trimethylsilyl bromide; Amberlite IR 120; di(n-butyl)tin oxide; acetic acid; 3-chloro-benzenecarboperoxoic acid; camphor-10-sulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00047a049

Reference yield:

methyl shikimate (40983-58-2) → Methyl 4,5-O-diacetyl-(-)-shikimate 3-phosphate (1053643-69-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / camphorsulfonic acid / 0.25 h / Ambient temperature

2: 100 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

3: 94 percent / aq. HOAc / tetrahydrofuran / 6 h / 70 °C

4: 1.) dibutyltin oxide / 1.) benzene, reflux, 1 h, 2.) DMF, 30 min

5: 100 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 1 h / 50 °C

6: 89 percent / 80percent aq. HOAc / 0.25 h

7: tetrazole / CH₂Cl₂ / 2 h / Ambient temperature

8: 0.304 g / m-CPBA / CH₂Cl₂ / 2 h / -40 °C

9: 80 percent / bromotrimethylsilane / CH₂Cl₂ / 1 h / 0 °C

With 1H-tetrazole; dmap; trimethylsilyl bromide; di(n-butyl)tin oxide; acetic acid; 3-chloro-benzenecarboperoxoic acid; camphor-10-sulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00047a049

upstream raw materials:

Methyl 4,5-O-diacetyl-(-)-shikimate dibenzyl 3-phosphate

methyl 3,4-O-isopropylideneshikimate

shikimic acid

methyl shikimate

Downstream raw materials:

(-)-shikimate 3-phosphate trisodium salt