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

Base Information

Chemical Name:Methyl 4,5-O-diacetyl-(-)-shikimate dibenzyl 3-phosphate
CAS No.:143308-78-5
Molecular Formula:C₂₆H₂₉O₁₀P
Molecular Weight:532.484
Hs Code.:

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

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

Chemical Property:

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

There total 8 articles about Methyl 4,5-O-diacetyl-(-)-shikimate dibenzyl 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:

: (3R,4S,5R)-4,5-Diacetoxy-3-(bis-benzyloxy-phosphanyloxy)-cyclohex-1-enecarboxylic acid methyl ester

: 143308-78-5
Methyl 4,5-O-diacetyl-(-)-shikimate dibenzyl 3-phosphate

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -40 ℃; for 2h;
DOI:10.1021/jo00047a049

Reference yield:

: 138-59-0
shikimic acid

: 143308-78-5
Methyl 4,5-O-diacetyl-(-)-shikimate dibenzyl 3-phosphate

Guidance literature:: Multi-step reaction with 9 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

With 1H-tetrazole; dmap; 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:

: 40983-58-2
methyl shikimate

: 143308-78-5
Methyl 4,5-O-diacetyl-(-)-shikimate dibenzyl 3-phosphate

Guidance literature:: Multi-step reaction with 8 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

With 1H-tetrazole; dmap; di(n-butyl)tin oxide; acetic acid; 3-chloro-benzenecarboperoxoic acid; camphor-10-sulfonic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00047a049