4'-Demethylepipodophyllotoxin

Base Information

• Chemical Name: 4'-Demethylepipodophyllotoxin
• CAS No.: 6559-91-7
• Molecular Formula: C21H20O8
• Molecular Weight: 400.385
• Hs Code.: 29349990
• UNII: X0S6I23X6L
• DSSTox Substance ID: DTXSID7048742
• Nikkaji Number: J49.608A
• Wikidata: Q27144659
• Metabolomics Workbench ID: 144379
• ChEMBL ID: CHEMBL31929
• Mol file: 6559-91-7.mol

Synonyms:4'-demethyl epipodophyllotoxin;4'-demethylepipodophyllotoxin

Chemical Property of 4'-Demethylepipodophyllotoxin

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 246-248 °C
• Boiling Point: 626.5 °C at 760 mmHg
• PKA: 9.94±0.40(Predicted)
• Flash Point: 224.4 °C
• PSA: 103.68000
• Density: 1.446 g/cm³
• LogP: 2.10620
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 400.11581759
• Heavy Atom Count: 29
• Complexity: 614

Purity/Quality:

99% ^*data from raw suppliers

4''-Demethylepipodophyllotoxin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O
• Isomeric SMILES: COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@@H](C4=CC5=C(C=C24)OCO5)O
• Uses: A potent inhibitor of microtubule assembly.

Technology Process of 4'-Demethylepipodophyllotoxin

There total 22 articles about 4'-Demethylepipodophyllotoxin 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: 89.0%

Carbonic acid benzyl ester 4-((5R,5aR,8aR)-6,9-dioxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester (156350-44-6) → 4'-demethylepipodophyllotoxin (6559-91-7)

Guidance literature:

With ruthenium(II) chloride; (S)-N₂,N₂'-bis(pyridin-2-ylmethyl-1,1'-binaphthyl-2,2'-diamine); hydrogen; In isopropyl alcohol; at 20 - 25 ℃; for 18h; under 38002.6 Torr;

Reference yield: 71.0%

4'-O-demethyl-4β-bromo-4-desoxypodophyllotoxin (16477-16-0) → 4'-demethylepipodophyllotoxin (6559-91-7)

Guidance literature:

With water; barium carbonate; In acetone; at 40 ℃; for 4h;

DOI:10.3891/acta.chem.scand.47-1190

Reference yield: 54.0%

→ 4'-demethylepipodophyllotoxin (6559-91-7)

Guidance literature:

upstream raw materials:

4'-O-demethyl-4β-bromo-4-desoxypodophyllotoxin

acetic acid

podofilox

1α-bromo-desoxypodophyllotoxin

Downstream raw materials:

4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4'-demethylepipodophyllotoxin

4-O-(2’,3’,4’,6’-tetra-O-acetyl-α-D-glucopyranosyl)-4-demethylepipodophyllotoxin

4β-azido-4-deoxy-4′-demethylepipodophyllotoxin

6,7-O,O-demethylene-4'-O-demethylepipodophyllotoxin

Refernces

• 1、 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.
• 2、 -. "Biotin-podophyllotoxin derivative and its pharmaceutical compositions and methods for their preparation and use". Paragraph 0040-0041. . Retrieved 2016/10/10.