Picropodophyllotoxin acetate

Base Information

• Chemical Name: Picropodophyllotoxin acetate
• CAS No.: 38491-90-6
• Molecular Formula: C24H24O9
• Molecular Weight: 456.449
• NSC Number: 31708
• DSSTox Substance ID: DTXSID20959364
• Nikkaji Number: J556.523E
• Wikidata: Q82940082
• Metabolomics Workbench ID: 135304
• ChEMBL ID: CHEMBL454333
• Mol file: 38491-90-6.mol

Synonyms:PICROPODOPHYLLOTOXIN ACETATE;38491-90-6;SR-05000002684;Picropodophyllin, acetate;Spectrum_001662;Spectrum2_000807;Spectrum3_000662;Spectrum4_001634;Spectrum5_000447;BSPBio_002323;KBioGR_002067;KBioSS_002142;SPECTRUM1504411;PICROPODOPHYLLIN ACETATE;SPBio_000673;CHEMBL454333;SCHEMBL4276054;KBio2_002142;KBio2_004710;KBio2_007278;KBio3_001543;DTXSID20959364;NSC31708;NSC-31708;CCG-214618;SDCCGMLS-0066752.P001;NCGC00161924-01;NCGC00161924-02;SR-05000002684-1;SR-05000002684-2;BRD-K99108905-001-02-0;8-Oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl acetate

Chemical Property of Picropodophyllotoxin acetate

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 456.14203234
• Heavy Atom Count: 33
• Complexity: 729

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C2COC(=O)C2C(C3=CC4=C(C=C13)OCO4)C5=CC(=C(C(=C5)OC)OC)OC
• Isomeric SMILES: CC(=O)O[C@@H]1[C@H]2COC(=O)[C@H]2[C@@H](C3=CC4=C(C=C13)OCO4)C5=CC(=C(C(=C5)OC)OC)OC

Technology Process of Picropodophyllotoxin acetate

There total 7 articles about Picropodophyllotoxin acetate 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:

acetic anhydride (108-24-7) + picropodophyllotoxin (477-47-4) → (5R,5aR,8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl acetate (38491-90-6)

Guidance literature:

With pyridine;

DOI:10.1021/ja01651a113 DOI:10.1021/ja01492a047

Reference yield:

podofilox (518-28-5) → (5R,5aR,8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl acetate (38491-90-6)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; palladium

2: sodium acetate

With methanol; sodium acetate; palladium;

Reference yield:

podophyllotoxinyl acetate (1180-34-3) → (5R,5aR,8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl acetate (38491-90-6)

Guidance literature:

With sodium acetate; acetic anhydride;

DOI:10.1021/ja01150a143

upstream raw materials:

podophyllotoxinyl acetate

sodium acetate

acetic anhydride

picropodophyllotoxin

Downstream raw materials:

4-O-acetyl-3',4'-didemethoxy-3',4'-dihydro-3',4'-dioxopodophyllotoxin

Refernces