4-benzoyloxy-3-hydroxymethyl-1-(3',4'-methylenedioxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-2-naphthoic acid γ-lactone

Base Information

• Chemical Name: 4-benzoyloxy-3-hydroxymethyl-1-(3',4'-methylenedioxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-2-naphthoic acid γ-lactone
• CAS No.: 103844-14-0
• Molecular Formula: C₂₈H₂₄O₈
• Molecular Weight: 488.494
• Mol file: 103844-14-0.mol

Synonyms:

Chemical Property of 4-benzoyloxy-3-hydroxymethyl-1-(3',4'-methylenedioxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-2-naphthoic acid γ-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-benzoyloxy-3-hydroxymethyl-1-(3',4'-methylenedioxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-2-naphthoic acid γ-lactone

There total 11 articles about 4-benzoyloxy-3-hydroxymethyl-1-(3',4'-methylenedioxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-2-naphthoic acid γ-lactone 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: 30.0%

erythro-3-(α-benzoyloxy-3'',4''-dimethoxybenzyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)-γ-butyrolactone (118825-98-2,118917-47-8,144539-71-9) → 4-benzoyloxy-3-hydroxymethyl-1-(3',4'-methylenedioxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-2-naphthoic acid γ-lactone (103844-14-0,118917-48-9)

Guidance literature:

With trimethoxonium tetrafluoroborate;

DOI:10.1016/S0040-4039(01)84603-7

Reference yield:

erythro-3-(α-benzoyloxy-3'',4''-dimethoxybenzyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)-γ-butyrolactone (118825-98-2,118917-47-8,144539-71-9) → 4-(3',4'-dimethoxyphenyl)-3-hydroxymethyl-6,7-methylenedioxy-3,4-dihydro-2-naphthoic acid γ-lactone (103844-18-4,118626-89-4) + 4-benzoyloxy-3-hydroxymethyl-1-(3',4'-methylenedioxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-2-naphthoic acid γ-lactone (103844-14-0,118917-48-9)

Guidance literature:

With Methyl fluorosulfonate; potassium carbonate; In dichloromethane; for 20h; Ambient temperature;

Reference yield:

3-(3'',4''-dimethoxybenzoyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)butyrolactone (103865-35-6,118917-44-5) → 4-benzoyloxy-3-hydroxymethyl-1-(3',4'-methylenedioxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-2-naphthoic acid γ-lactone (103844-14-0,118917-48-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / NaBH₄ / methanol / 4 h / 0 °C

2: 86 percent / BuLi / tetrahydrofuran / 2 h / -78 deg C to room temperature

3: 29 percent / K₂CO₃, FSO₃Me / CH₂Cl₂ / 20 h / Ambient temperature

With Methyl fluorosulfonate; sodium tetrahydroborate; n-butyllithium; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

erythro-3-(α-benzoyloxy-3'',4''-dimethoxybenzyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)-γ-butyrolactone

3-(3'',4''-dimethoxybenzoyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)butyrolactone

erythro-3-(α-hydroxy-3'',4''-dimethoxybenzyl)-2-(3,4-methylenedioxy-α-phenylthiobenzyl)-γ-butyrolactone

piperonal