Lignan P

Base Information

• Chemical Name: Lignan P
• CAS No.: 23363-35-1
• Molecular Formula: C27H30O13
• Molecular Weight: 562.527
• UNII: C2G3ZRK3U4
• DSSTox Substance ID: DTXSID60946031
• Nikkaji Number: J2.839.131E
• Wikidata: Q27275102
• Metabolomics Workbench ID: 124534
• ChEMBL ID: CHEMBL1778161
• Mol file: 23363-35-1.mol

Synonyms:4'-demethylepipodophyllotoxin-9 beta-glucopyranoside;4'-demethylepipodophyllotoxin-9 beta-glucopyranoside, (9alpha)-isomer

Chemical Property of Lignan P

Chemical Property:

• Melting Point: 262-264 °C(Solv: methanol (67-56-1))
• Boiling Point: 808.2 °C at 760 mmHg
• PKA: 9.94±0.40(Predicted)
• Flash Point: 270.4 °C
• PSA: 182.83000
• Density: 1.62 g/cm³
• LogP: -0.06960
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 6
• Exact Mass: 562.16864101
• Heavy Atom Count: 40
• Complexity: 892

Purity/Quality:

98%,99%, ^*data from raw suppliers

LignanP ^*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)OC6C(C(C(C(O6)CO)O)O)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[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• Uses: Lignan P, is a metabolite of Etoposide (E933750), which is a DNA topoisomerase II inhibitor. Semi-synthetic derivative of podophyllotoxin, related structurally to Teniposide. It is also an Antineoplastic. Lignan P is a metabolite of Etoposide (E933750), which is a DNA topoisomerase II inhibitor. Semi-synthetic derivative of podophyllotoxin, related structurally to Teniposide. It is also an Antineoplastic.

Technology Process of Lignan P

There total 5 articles about Lignan P 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: 70.0%

4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4'-demethylepipodophyllotoxin (23363-34-0) → 4-demethylepipodophyllotoxin-7'-O-β-D-glucopyranoside (23363-35-1)

Guidance literature:

With methanol; zinc diacetate; for 40h; Heating;

DOI:10.1016/S0040-4039(00)61297-2

Reference yield: 69.0%

etoposide (33419-42-0) → 4-demethylepipodophyllotoxin-7'-O-β-D-glucopyranoside (23363-35-1)

Guidance literature:

With acetic acid; In water; at 68 - 72 ℃; for 20h;

DOI:10.1016/S0968-0896(01)00102-X

Reference yield:

2,3,4,6-tetra-O-acetyl-β-D-glucopyranose (3947-62-4) → 4-demethylepipodophyllotoxin-7'-O-β-D-glucopyranoside (23363-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / -20 °C

2: 70 percent / Zn(OAc)2, MeOH / 40 h / Heating

With methanol; boron trifluoride diethyl etherate; zinc diacetate; In dichloromethane;

DOI:10.1016/S0040-4039(00)61297-2

upstream raw materials:

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

etoposide

4'-demethylepipodophyllotoxin

2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Downstream raw materials:

4'-demethyl-1-O-[4,6-O-(4-azido-5-iodo-2-methoxybenzylidene)-β-D-glucopyranosyl]epipodophyllotoxin

etoposide

Refernces

• 1、 Allevi, Pietro,Anastasia, Mario,Ciuffreda, Pierangela,Sanvito, Anna Maria,Macdonald, Peter. "A Short and Simple Synthesis of the Antitumor Agent Etoposide". . p. 4831 - 4834. Retrieved 2007/10/02.