(4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carboxylic acid

Base Information

• Chemical Name: (4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carboxylic acid
• CAS No.: 79289-93-3
• Molecular Formula: C₂₅H₂₈O₉
• Molecular Weight: 472.492
• Mol file: 79289-93-3.mol

Synonyms:

Chemical Property of (4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carboxylic acid

There total 18 articles about (4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-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: 83.0%

(4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carboxylic acid methyl ester (79305-58-1,86334-70-5) → (4aR,5R,6S,11bS)-2,2-Dimethyl-6-(3,4,5-trimethoxy-phenyl)-4a,5,6,11b-tetrahydro-4H-1,3,8,10-tetraoxa-cyclopenta[b]phenanthrene-5-carboxylic acid (79289-93-3,86334-71-6)

Guidance literature:

With potassium hydroxide; In 1,4-dioxane; water; for 4h; Heating;

DOI:10.1139/v83-101

Reference yield: 82.0%

methyl epipodophyllate 4,11-acetonide (79305-58-1,86334-70-5) → epipodophyllic acid 4,11-acetonide (79289-93-3,86334-71-6)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; for 6h; Heating;

DOI:10.1021/ja00410a038

Reference yield:

(+/-)-methyl epipodophyllate (1256-91-3,55515-12-3,75171-58-3,78216-03-2,86334-69-2,116180-67-7,122871-76-5,127126-86-7) → epipodophyllic acid 4,11-acetonide (79289-93-3,86334-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / p-toluenesulfonic acid

2: 82 percent / NaOH / H₂O; dioxane / 6 h / Heating

With sodium hydroxide; toluene-4-sulfonic acid; In 1,4-dioxane; water;

DOI:10.1021/ja00410a038

upstream raw materials:

methyl epipodophyllate 4,11-acetonide

(+/-)-methyl epipodophyllate

C₂₃H₂₄O₉

piperonal

Downstream raw materials:

(+/-)-neopodophyllotoxin

epipodophyllic acid

9-hydroxy-5-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-5aH-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

(+/-)-epipodophyllotoxin