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

Base Information

• Chemical Name: erythro-3-(α-benzoyloxy-3'',4''-dimethoxybenzyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)-γ-butyrolactone
• CAS No.: 118825-98-2
• Molecular Formula: C₃₄H₃₀O₈S
• Molecular Weight: 598.673
• Mol file: 118825-98-2.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about erythro-3-(α-benzoyloxy-3'',4''-dimethoxybenzyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)-γ-butyrolactone 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: 86.0%

benzoyl chloride (98-88-4) + erythro-3-(α-hydroxy-3'',4''-dimethoxybenzyl)-2-(3,4-methylenedioxy-α-phenylthiobenzyl)-γ-butyrolactone (118825-97-1,118917-46-7,144539-70-8) → erythro-3-(α-benzoyloxy-3'',4''-dimethoxybenzyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)-γ-butyrolactone (118825-98-2,118917-47-8,144539-71-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; for 2h; -78 deg C to room temperature;

Reference yield:

3-(3'',4''-dimethoxybenzoyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)butyrolactone (103865-35-6,118917-44-5) → erythro-3-(α-benzoyloxy-3'',4''-dimethoxybenzyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)-γ-butyrolactone (118825-98-2,118917-47-8,144539-71-9)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium tetrahydroborate; n-butyllithium; In tetrahydrofuran; methanol;

Reference yield:

piperonal (120-57-0,30024-74-9) → erythro-3-(α-benzoyloxy-3'',4''-dimethoxybenzyl)-2-(3',4'-methylenedioxy-α-phenylthiobenzyl)-γ-butyrolactone (118825-98-2,118917-47-8,144539-71-9)

Guidance literature:

Multi-step reaction with 3 steps

2: conc. aqueous perchloric acid

3: 1.) NaBH₄, 2.) BuLi

With sodium tetrahydroborate; n-butyllithium; perchloric acid;

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

upstream raw materials:

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

benzoyl chloride

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

piperonal

Downstream raw materials:

retrochinensin

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

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

4-(3',4'-dimethoxyphenyl)-3-hydroxymethyl-6,7-methylenedioxy-3,4-dihydro-2-naphthoic acid γ-lactone

Refernces

• 1、 Pelter, Andrew,Ward, Robert S.,Pritchard, Martyn C.,Kay, I. Trevor. "SYNTHESIS OF DEOXYISOPODOPHYLLOTOXIN AND EPIISOPODOPHYLLOTOXIN.". . p. 6377 - 6380. Retrieved 2007/10/02.