(±)-β-apopicropodophyllin

Base Information

• Chemical Name: (±)-β-apopicropodophyllin
• CAS No.: 59123-24-9
• Molecular Formula: C₂₂H₂₀O₇
• Molecular Weight: 396.397
• Mol file: 59123-24-9.mol

Synonyms:(±)-β-apopicropodophyllin

Chemical Property of (±)-β-apopicropodophyllin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (±)-β-apopicropodophyllin

There total 25 articles about (±)-β-apopicropodophyllin 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: 90.0%

Podophyllotoxin (477-47-4,518-28-5,4354-76-1,4375-06-8,4375-07-9,26540-82-9,55568-79-1,55568-80-4,60660-50-6,62319-21-5,77519-37-0,77519-38-1,79355-67-2,86334-73-8,118627-04-6,122871-77-6,122871-79-8,122871-81-2) → (±)-β-apopicropodophyllin (59123-24-9)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; for 10h; Heating;

Reference yield: 88.0%

4-benzyl-5-ethoxyoxazole (33318-75-1) + C24H27F3O8SSi → (±)-β-apopicropodophyllin (59123-24-9)

Guidance literature:

4-benzyl-5-ethoxyoxazole; C₂₄H₂₇F₃O₈SSi; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -78 - -20 ℃; for 1h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; diethyl ether; water; at 20 ℃;

DOI:10.1021/acs.orglett.8b02398

Reference yield: 39.0%

1-[7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,8-dihydro-naphtho[2,3-d][1,3]dioxol-6-yl]-ethane-1,2-diol → (±)-β-apopicropodophyllin (59123-24-9) + 5-(3,4,5-trimethoxy-phenyl)-5,9-dihydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole

Guidance literature:

1-[7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,8-dihydro-naphtho[2,3-d][1,3]dioxol-6-yl]-ethane-1,2-diol; With lead(IV) acetate; sodium hydrogencarbonate; In dichloromethane; at 0 ℃; for 0.25h;

With dipyridinium dichromate; In dichloromethane; for 0.5h;

DOI:10.1021/ol049649p

upstream raw materials:

Podophyllotoxin

sulfuric acid

(+/-)-isopodophyllinic acid

water

Downstream raw materials:

(+/-)-α-apopicropodophyllinic acid

Refernces

• 1、 Lisiecki, Kamil,Krawczyk, Krzysztof K.,Roszkowski, Piotr,Maurin, Jan K.,Budzianowski, Armand,Czarnocki, Zbigniew. "Unusual visible-light photolytic cleavage of tertiary amides during the synthesis of cyclolignans related to podophyllotoxin". . p. 6316 - 6328. Retrieved 2017/10/06.
• 2、 Anjanamurthy, C.,Lokanatha Rai, K. M.. "A New One-Step Preparation of β-Apopicropodophyllin from Podophyllotoxin". . p. 62 - 63. Retrieved 2007/10/02.