aceroside IV perbenzoate

Base Information

• Chemical Name: aceroside IV perbenzoate
• CAS No.: 197382-99-3
• Molecular Formula: C₅₃H₄₆O₁₂
• Molecular Weight: 874.941
• Mol file: 197382-99-3.mol

Synonyms:aceroside IV perbenzoate

Chemical Property of aceroside IV perbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of aceroside IV perbenzoate

There total 15 articles about aceroside IV perbenzoate 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: 93.0%

2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2) + 12-oxo-2-oxatricyclo[13.2.2.13,7]eicosa-1(18),3(20),4,6,15(19),16-hexaen-4-ol (87425-32-9) → aceroside IV perbenzoate (197382-99-3)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1021/jo981844s

Reference yield:

3-(3-hydroxy-4-methoxyphenyl)-propionic acid methyl ester (129150-61-4) → aceroside IV perbenzoate (197382-99-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 96 percent / K₂CO₃ / dimethylformamide / 24 h / 60 °C

2.1: 97 percent / LAH / tetrahydrofuran / 45 h / 0 °C

3.1: pyridine / 20 °C

4.1: 1.31 g / NaI / acetone / Heating

5.1: LDA / tetrahydrofuran / 0.33 h / 0 °C

5.2: 80 percent / tetrahydrofuran / 0.33 h / 0 °C

6.1: NaH / tetrahydrofuran / 0.33 h / 0 °C

6.2: 76 percent / tetrahydrofuran / 1 h / 0 °C

7.1: BCl₃ / CH₂Cl₂ / 1 h / 0 °C

8.1: 1.25 g / aq. HCl / 24 h / Heating

9.1: 95 percent / CsF / dimethylformamide / 5 h / 20 °C

10.1: 100 percent / H₂ / Pd/C / methanol / 1 h

11.1: 90 percent / tert-butyl nitrite / dimethylformamide / 1 h / 50 °C

12.1: 88 percent / AlCl₃ / CH₂Cl₂ / 18 h / Heating

13.1: 93 percent / aq. NaOH; tetrabutylammonium bromide / CH₂Cl₂ / 5 h / 20 °C

With pyridine; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; tert.-butylnitrite; tetrabutylammomium bromide; hydrogen; boron trichloride; sodium hydride; potassium carbonate; cesium fluoride; sodium iodide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 1.1: Etherification / 2.1: Reduction / 3.1: Tosylation / 4.1: Substitution / 5.1: Metallation / 5.2: Alkylation / 6.1: Metallation / 6.2: Alkylation / 7.1: dealkylation / 8.1: Decarboxylation / 9.1: Cyclization / 10.1: Hydrogenolysis / 11.1: Deamination / 12.1: demethylation / 13.1: glycosidation;

DOI:10.1021/jo981844s

Reference yield:

4-fluoro-3-nitrobenzyl iodide (221123-51-9) → aceroside IV perbenzoate (197382-99-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 0.33 h / 0 °C

1.2: 76 percent / tetrahydrofuran / 1 h / 0 °C

2.1: BCl₃ / CH₂Cl₂ / 1 h / 0 °C

3.1: 1.25 g / aq. HCl / 24 h / Heating

4.1: 95 percent / CsF / dimethylformamide / 5 h / 20 °C

5.1: 100 percent / H₂ / Pd/C / methanol / 1 h

6.1: 90 percent / tert-butyl nitrite / dimethylformamide / 1 h / 50 °C

7.1: 88 percent / AlCl₃ / CH₂Cl₂ / 18 h / Heating

8.1: 93 percent / aq. NaOH; tetrabutylammonium bromide / CH₂Cl₂ / 5 h / 20 °C

With hydrogenchloride; sodium hydroxide; aluminium trichloride; tert.-butylnitrite; tetrabutylammomium bromide; hydrogen; boron trichloride; sodium hydride; cesium fluoride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Alkylation / 2.1: dealkylation / 3.1: Decarboxylation / 4.1: Cyclization / 5.1: Hydrogenolysis / 6.1: Deamination / 7.1: demethylation / 8.1: glycosidation;

DOI:10.1021/jo981844s

upstream raw materials:

2,3,4,6-tetra-O-benzoylglucosyl bromide

12-oxo-2-oxatricyclo[13.2.2.1^3,7]eicosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaen-4-ol

4-methoxy-2-oxatricyclo[13.2.2.1^3,7]eicosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaen-12-one

4-fluoro-3-nitrobenzyl iodide