Etoposidephosphate

Base Information

• Chemical Name: Etoposidephosphate
• CAS No.: 117091-64-2
• Molecular Formula: C₂₉H₃₃O₁₆P
• Molecular Weight: 668.545
• Hs Code.: 2938909090
• European Community (EC) Number: 630-364-1
• Mol file: 117091-64-2.mol

Synonyms:ETOPOSIDEPHOSPHATE;117091-64-2;[4-[5-[(7,8-Dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy]-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-9-yl]-2,6-dimethoxyphenyl] dihydrogen phosphate;DB-041349;4-[16-({7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl}oxy)-12-oxo-4,6,13-trioxatetracyclo[7.7.0.0(3),?.0(1)(1),(1)?]hexadeca-1,3(7),8-trien-10-yl]-2,6-dimethoxyphenoxyphosphonic acid

Chemical Property of Etoposidephosphate

Chemical Property:

• Boiling Point: 798.1 °C at 760 mmHg
• PKA: 1.13±0.50(Predicted)
• Flash Point: 263.6 °C
• PSA: 217.17000
• Density: 1.55 g/cm³
• LogP: 1.10450
• Storage Temp.: -20°C
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 7
• Exact Mass: 668.15062196
• Heavy Atom Count: 46
• Complexity: 1140

Purity/Quality:

99% ^*data from raw suppliers

Etoposide Phosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1OCC2C(O1)C(C(C(O2)OC3C4COC(=O)C4C(C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)OP(=O)(O)O)OC)O)O
• Uses: As a bioequivalent prodrug of the DNA topoisomerase II inhibitor Etoposide (E933750), Etoposide phosphate can be used in the treatment of a wide variety of hematological malignancies and solid tumors.

Technology Process of Etoposidephosphate

There total 6 articles about Etoposidephosphate 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: 87.4%

dibenzyl 4-(2,3-di-O-benzyl-4,6-O-ethylidene-β-D-glucopyranosyl)-4'-demethyl-4-epipodophyllotoxin-4'-phosphate → etoposide phosphate (117091-64-2)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20 ℃; for 4h; under 3087.28 Torr; Autoclave; Inert atmosphere;

Reference yield:

water-methanol + etoposide (33419-42-0) + octadecyl silane (18623-11-5) → etoposide phosphate (117091-64-2)

Guidance literature:

With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In methanol; water; ethyl acetate; acetonitrile;

Reference yield:

4'-demethylepipodophyllotoxin (6559-91-7) → etoposide phosphate (117091-64-2)

Guidance literature:

Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine; dmap / acetonitrile; tetrachloromethane / -10 °C / Inert atmosphere

2: boron trifluoride diethyl etherate / acetonitrile / -40 °C / Inert atmosphere

3: 5%-palladium/activated carbon; hydrogen / methanol; tetrahydrofuran / 4 h / 20 °C / 3087.28 Torr / Autoclave; Inert atmosphere

With dmap; 5%-palladium/activated carbon; boron trifluoride diethyl etherate; hydrogen; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; tetrachloromethane; acetonitrile;

upstream raw materials:

etoposide

octadecyl silane

4'-demethylepipodophyllotoxin

Refernces

• 1、 -. "Etoposide phosphate and preparative intermediates". . . Retrieved 2008/06/13.