(6S)-7-methylidene-8-oxo-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylic acid

Base Information

• Chemical Name: (6S)-7-methylidene-8-oxo-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylic acid
• CAS No.: 120090-82-6
• Molecular Formula: C22H20 O8
• Molecular Weight: 412.3894
• Mol file: 120090-82-6.mol

Synonyms:Naphtho[2,3-d]-1,3-dioxole-6-carboxylicacid, 5,6,7,8-tetrahydro-7-methylene-8-oxo-5-(3,4,5-trimethoxyphenyl)-,(5R-trans)-; Thuriferic acid

Chemical Property of (6S)-7-methylidene-8-oxo-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylic acid

Chemical Property:

• Vapor Pressure: 6.98E-14mmHg at 25°C
• Boiling Point: 571.1°Cat760mmHg
• Flash Point: 199.1°C
• Density: 1.41g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (6S)-7-methylidene-8-oxo-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylic acid

There total 6 articles about (6S)-7-methylidene-8-oxo-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylic acid 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:

podophyllotoxone (477-48-5,477-49-6,55515-07-6,60660-51-7,64550-42-1,64937-82-2,86594-36-7,130322-38-2) → thuriferic acid (120090-82-6)

Guidance literature:

With potassium hydroxide; In methanol; for 0.5h; Ambient temperature;

DOI:10.1016/0040-4020(95)00275-D

Reference yield:

(5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione (477-48-5) → thuriferic acid (120090-82-6)

Guidance literature:

With potassium tert-butylate; water; In tert-butyl alcohol; for 0.166667h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4020(01)86096-8

Reference yield:

podofilox (518-28-5) → thuriferic acid (120090-82-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / PDC / CH₂Cl₂ / 3 h / 20 °C

2: 670 mg / KOH / methanol / 0.5 h / 20 °C

With potassium hydroxide; dipyridinium dichromate; In methanol; dichloromethane;

DOI:10.1016/j.tet.2005.11.068

upstream raw materials:

(5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione

podophyllotoxone

podofilox

picropodophyllotoxin

Downstream raw materials:

thuriferic acid methyl ester

(1R,2S,3R)-N-(4-bromophenyl)-picropodophyllone-cis-γ-lactam

(1R,2S,3R)-N-(3-bromophenyl)-picropodophyllone-cis-γ-lactam

8-oxo-7-(p-tolylamino-methyl)-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester

Refernces

• 1、 Del Corral,Gordaliza,Lopez,Del Olmo,Castro,Lopez. "Reassignment of the configuration of several keto-cyclolignans prepared from podophyllotoxin". . p. 1793 - 1796. Retrieved 1995.
• 2、 Dorbec, Matthieu,Florent, Jean-Claude,Monneret, Claude,Rager, Marie-No?lle,Bertounesque, Emmanuel. "Synthesis of γ-lactam lignans via aza-Michael addition". . p. 591 - 594. Retrieved 2007/10/03.