(+/-)-isopodophyllotoxone

Base Information

• Chemical Name: (+/-)-isopodophyllotoxone
• CAS No.: 130322-38-2
• Molecular Formula: C₂₂H₂₀O₈
• Molecular Weight: 412.396
• Mol file: 130322-38-2.mol

Synonyms:

Chemical Property of (+/-)-isopodophyllotoxone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-isopodophyllotoxone

There total 50 articles about (+/-)-isopodophyllotoxone 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: 100.0%

(5aR,8aR,9R)-5,8-Dioxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester (620116-57-6) → (1α,2α,3α)-podophyllotoxin (55515-07-6,477-48-5,477-49-6,60660-51-7,64550-42-1,64937-82-2,86594-36-7,130322-38-2)

Guidance literature:

With palladium diacetate; formic acid; triphenylphosphine; NEt₂; In tetrahydrofuran; at 25 ℃; for 0.716667h;

DOI:10.1021/ja0376588

Reference yield: 95.0%

(-)-4-desoxy-4-methylenepodophyllotoxin → 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)

Guidance literature:

(-)-4-desoxy-4-methylenepodophyllotoxin; With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 4h;

With sodium periodate; In dichloromethane; for 0.5h;

DOI:10.1002/anie.200802611

Reference yield: 92.0%

podofilox (518-28-5) → 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)

Guidance literature:

With dipyridinium dichromate; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.bmc.2014.07.031

upstream raw materials:

podofilox

podophyllotoxinyl acetate

podophyllotoxin-7′-O-β-D-glucopyranoside

deoxypodophyllotoxin

Downstream raw materials:

dehydropodophyllotoxin

(3aR)-2-phenyl-5c-(3,4,5-trimethoxy-phenyl)-(3ar)-3,3a,4,5-tetrahydro-2H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]indazole-4c-carboxylic acid

(1α,2α,3α)-podophyllotoxin

<5R-(5α,6α)>-5,6,7,8-tetrahydro-7-methylidene-8-oxo-5-(3,4,5-trimethoxyphenyl)naphtho<2,3-d><1,3>dioxole-6-carboxylic acid

Refernces

• 1、 Dewick, Paul M.,Jackson, David E.. "CYTOTOXIC LIGNANS FROM PODOPHYLLUM, AND THE NOMENCLATURE OF ARYLTETRALIN LIGNANS". . p. 2277 - 2280. Retrieved 1981.
• 2、 Kamal, Ahmed,Damayanthi. "A novel enzymatic dehydrogenation of podophyllotoxin congeners by yeast cells". . p. 657 - 662. Retrieved 1997.
• 3、 Ara, T.,Banday, J. A.,Bhat, B. A.,Ganaie, B. A.. "Synthesis and In Vitro Anticancer Activity of Triazolyl Analogs of Podophyllotoxin, a Naturally Occurring Lignin". . p. 2039 - 2047. Retrieved 2022/01/24.
• 4、 Ye, Danfeng,Liu, Zhiyuan,Sessler, Jonathan L.,Lei, Chuanhu. "Base-free oxidation of alcohols enabled by nickel(ii)-catalyzed transfer dehydrogenation". supporting information. p. 11811 - 11814. Retrieved 2020/10/13.