8-Benzyloxy-2-((3S,4S,5R)-6-hydroxy-4-methoxy-3,5-dimethyl-hexyl)-5,7-dimethoxy-3-methyl-chromen-4-one

Base Information

• Chemical Name: 8-Benzyloxy-2-((3S,4S,5R)-6-hydroxy-4-methoxy-3,5-dimethyl-hexyl)-5,7-dimethoxy-3-methyl-chromen-4-one
• CAS No.: 293744-14-6
• Molecular Formula: C₂₈H₃₆O₇
• Molecular Weight: 484.59
• Mol file: 293744-14-6.mol

Synonyms:8-Benzyloxy-2-((3S,4S,5R)-6-hydroxy-4-methoxy-3,5-dimethyl-hexyl)-5,7-dimethoxy-3-methyl-chromen-4-one

Chemical Property of 8-Benzyloxy-2-((3S,4S,5R)-6-hydroxy-4-methoxy-3,5-dimethyl-hexyl)-5,7-dimethoxy-3-methyl-chromen-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-Benzyloxy-2-((3S,4S,5R)-6-hydroxy-4-methoxy-3,5-dimethyl-hexyl)-5,7-dimethoxy-3-methyl-chromen-4-one

There total 19 articles about 8-Benzyloxy-2-((3S,4S,5R)-6-hydroxy-4-methoxy-3,5-dimethyl-hexyl)-5,7-dimethoxy-3-methyl-chromen-4-one 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:

3,4,5-trihydroxybenzoic acid (149-91-7) → 8-Benzyloxy-2-((3S,4S,5R)-6-hydroxy-4-methoxy-3,5-dimethyl-hexyl)-5,7-dimethoxy-3-methyl-chromen-4-one (293744-14-6)

Guidance literature:

Multi-step reaction with 13 steps

2.1: 32 percent / K₂CO₃ / dimethylformamide / 72 h / 80 °C

3.1: 100 percent / K₂CO₃ / dimethylformamide / 3 h / 0 °C

4.1: 97 percent / DIBAH / CH₂Cl₂ / 3 h / -78 °C

5.1: 76 percent / PCC / CH₂Cl₂ / 2 h / 20 °C

6.1: 30 percent aq. hydrogen peroxide; phenylselenic acid / CH₂Cl₂ / 48 h / 20 °C

6.2: KOH / methanol / 0.5 h / 20 °C

7.1: KOH / dimethylsulfoxide / 3 h / 20 °C

8.1: 100 percent / hydrogen / 20 percent Pd(OH)2/C / methanol / 18 h / 20 °C

9.1: 98 percent / pyridine / diethyl ether / 4 h / 20 °C

10.1: AlCl₃ / CH₂Cl₂ / 3 h / 20 °C

10.2: 94 percent / aq. HCl / methanol / 0.5 h / Heating

11.1: 60 percent / Huenig base / CH₂Cl₂ / 24 h / 20 °C

12.1: 77 percent / aq. K₂CO₃; n-Bu₃NHSO₄ / benzene / 20 h / 20 °C

13.1: NaH / dimethylsulfoxide / 3 h / 20 °C

13.2: aq. oxalic acid / 0 °C

13.3: AcOH; conc. HCl / 1.5 h

With pyridine; potassium hydroxide; aluminium trichloride; n-Bu₃NHSO₄; phenylselenate; hydrogen; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 1.1: Esterification / 2.1: Condensation / 3.1: Methylation / 4.1: Reduction / 5.1: Oxidation / 6.1: Oxidation / 6.2: Hydrolysis / 7.1: Methylation / 8.1: Hydrogenolysis / 9.1: Esterification / 10.1: Rearrangement / 10.2: Hydrolysis / 11.1: Alkylation / 12.1: Condensation / 13.1: Reduction / 13.2: Cyclization / 13.3: desilylation;

DOI:10.1016/S0040-4039(00)00812-1

Reference yield:

methyl galloate (99-24-1) → 8-Benzyloxy-2-((3S,4S,5R)-6-hydroxy-4-methoxy-3,5-dimethyl-hexyl)-5,7-dimethoxy-3-methyl-chromen-4-one (293744-14-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 32 percent / K₂CO₃ / dimethylformamide / 72 h / 80 °C

2.1: 100 percent / K₂CO₃ / dimethylformamide / 3 h / 0 °C

3.1: 97 percent / DIBAH / CH₂Cl₂ / 3 h / -78 °C

4.1: 76 percent / PCC / CH₂Cl₂ / 2 h / 20 °C

5.1: 30 percent aq. hydrogen peroxide; phenylselenic acid / CH₂Cl₂ / 48 h / 20 °C

5.2: KOH / methanol / 0.5 h / 20 °C

6.1: KOH / dimethylsulfoxide / 3 h / 20 °C

7.1: 100 percent / hydrogen / 20 percent Pd(OH)2/C / methanol / 18 h / 20 °C

8.1: 98 percent / pyridine / diethyl ether / 4 h / 20 °C

9.1: AlCl₃ / CH₂Cl₂ / 3 h / 20 °C

9.2: 94 percent / aq. HCl / methanol / 0.5 h / Heating

10.1: 60 percent / Huenig base / CH₂Cl₂ / 24 h / 20 °C

11.1: 77 percent / aq. K₂CO₃; n-Bu₃NHSO₄ / benzene / 20 h / 20 °C

12.1: NaH / dimethylsulfoxide / 3 h / 20 °C

12.2: aq. oxalic acid / 0 °C

12.3: AcOH; conc. HCl / 1.5 h

With pyridine; potassium hydroxide; aluminium trichloride; n-Bu₃NHSO₄; phenylselenate; hydrogen; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 1.1: Condensation / 2.1: Methylation / 3.1: Reduction / 4.1: Oxidation / 5.1: Oxidation / 5.2: Hydrolysis / 6.1: Methylation / 7.1: Hydrogenolysis / 8.1: Esterification / 9.1: Rearrangement / 9.2: Hydrolysis / 10.1: Alkylation / 11.1: Condensation / 12.1: Reduction / 12.2: Cyclization / 12.3: desilylation;

DOI:10.1016/S0040-4039(00)00812-1

Reference yield:

7-methoxy-2-phenyl-benzo[1,3]dioxol-5-ol (293744-00-0) → 8-Benzyloxy-2-((3S,4S,5R)-6-hydroxy-4-methoxy-3,5-dimethyl-hexyl)-5,7-dimethoxy-3-methyl-chromen-4-one (293744-14-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: KOH / dimethylsulfoxide / 3 h / 20 °C

2.1: 100 percent / hydrogen / 20 percent Pd(OH)2/C / methanol / 18 h / 20 °C

3.1: 98 percent / pyridine / diethyl ether / 4 h / 20 °C

4.1: AlCl₃ / CH₂Cl₂ / 3 h / 20 °C

4.2: 94 percent / aq. HCl / methanol / 0.5 h / Heating

5.1: 60 percent / Huenig base / CH₂Cl₂ / 24 h / 20 °C

6.1: 77 percent / aq. K₂CO₃; n-Bu₃NHSO₄ / benzene / 20 h / 20 °C

7.1: NaH / dimethylsulfoxide / 3 h / 20 °C

7.2: aq. oxalic acid / 0 °C

7.3: AcOH; conc. HCl / 1.5 h

With pyridine; potassium hydroxide; aluminium trichloride; n-Bu₃NHSO₄; hydrogen; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; benzene; 1.1: Methylation / 2.1: Hydrogenolysis / 3.1: Esterification / 4.1: Rearrangement / 4.2: Hydrolysis / 5.1: Alkylation / 6.1: Condensation / 7.1: Reduction / 7.2: Cyclization / 7.3: desilylation;

DOI:10.1016/S0040-4039(00)00812-1

upstream raw materials:

(4S,5S,6R)-5-Methoxy-4,6-dimethyl-7-triisopropylsilanyloxy-heptanoic acid 2-benzyloxy-3,5-dimethoxy-6-propionyl-phenyl ester

8-Benzyloxy-5,7-dimethoxy-2-((3S,4S,5R)-4-methoxy-3,5-dimethyl-6-triisopropylsilanyloxy-hexyl)-3-methyl-chromen-4-one

1,2-dihydroxy-3,5-dimethoxybenzene

3,4,5-trihydroxybenzoic acid

Downstream raw materials:

(2S,3S,4S)-6-(8-Benzyloxy-5,7-dimethoxy-3-methyl-4-oxo-4H-chromen-2-yl)-3-methoxy-2,4-dimethyl-hexanal

stigmatellin A

Refernces