Picropodopyllotoxone

Base Information

• Chemical Name: Picropodopyllotoxone
• CAS No.: 477-48-5
• Molecular Formula: C22H20O8
• Molecular Weight: 412.396
• DSSTox Substance ID: DTXSID40197246
• Nikkaji Number: J397.736F
• Wikidata: Q83070175
• Metabolomics Workbench ID: 143510
• ChEMBL ID: CHEMBL82303
• Mol file: 477-48-5.mol

Synonyms:Picropodopyllotoxone;PICROPODOPHYLLONE;477-48-5;Picropodopyllotoxon;(-)-Picropodopyllone;(5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxole-5,8-dione;5a,6,8a,9-Tetrahydro-9-(3,4,5-trimethoxyphenyl)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxole-5,8-dione (5aR-(5aalpha,8aalpha,9aalpha))-;Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxole-5,8-dione, 5a,6,8a,9-tetrahydro-9-(3,4,5-trimethoxyphenyl)-, (5aR-(5aalpha,8aalpha,9aalpha))-;C22H20O8;(5R)-5,8,8abeta,9-Tetrahydro-5beta-(3,4,5-trimethoxyphenyl)furo[3',4';CHEMBL82303;SCHEMBL18381519;DTXSID40197246;HY-N7684;AKOS040760634;MS-27118;CS-0135208

Chemical Property of Picropodopyllotoxone

Chemical Property:

• Boiling Point: 602.3°Cat760mmHg
• Flash Point: 263.5°C
• PSA: 89.52000
• Density: 1.365g/cm³
• LogP: 2.55850
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 412.11581759
• Heavy Atom Count: 30
• Complexity: 668

Purity/Quality:

Analysis control,HPLC≥98% ^*data from raw suppliers

Picropodophyllone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(=O)C4=CC5=C(C=C24)OCO5
• Isomeric SMILES: COC1=CC(=CC(=C1OC)OC)[C@H]2[C@H]3[C@H](COC3=O)C(=O)C4=CC5=C(C=C24)OCO5

Technology Process of Picropodopyllotoxone

There total 75 articles about Picropodopyllotoxone 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: 95.0%

picropodophyllotoxin (477-47-4) → (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)

Guidance literature:

With pyridine; chromium(VI) oxide; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1021/jf303069v

upstream raw materials:

picropodophyllotoxin

podophyllotoxinyl acetate

(-)-3-(hydroxymethyl)picropodophyllone

podophyllotoxone

Downstream raw materials:

C₂₂H₂₂O₈

thuriferic acid

(5R,6S,7S)-7-Methoxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid

picropodophyllotoxin

Refernces

• 1、 Arseniyadis, Stellios,Clavier, Louis,Copin, Chloé,Fournier, Jean,Giffard, Jean-Fran?ois,Jean, Alexandre,Katsina, Tania,Macedo Portela Da Silva, Nayane,Tamion, Rodolphe. "Scalable Aerobic Oxidation of Alcohols Using Catalytic DDQ/HNO3". supporting information. p. 856 - 860. Retrieved 2020/07/14.
• 2、 Kim, Eunae,Kim, Hyun Jung,Cho, Seung-Sik,Shim, Jung-Hyun,Yoon, Goo. "Isolation, Semisynthesis, and Molecular Modeling of Deoxypodophyllotoxin Analogs for an Anti-oral Cancer Agent". . p. 472 - 475. Retrieved 2020/02/13.