α-Etoposide

Base Information

• Chemical Name: α-Etoposide
• CAS No.: 100007-53-2
• Molecular Formula: C₂₉H₃₂O₁₃
• Molecular Weight: 588.565
• Mol file: 100007-53-2.mol

Synonyms:Etoposide Impurity C;alpha-Etoposide;(5R,5aR,8aR,9S)-9-[[4,6-O-(1R)-Ethylidene-alpha-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one

Chemical Property of α-Etoposide

Chemical Property:

• Boiling Point: 798.1±60.0 °C(Predicted)
• PKA: 9.94±0.40(Predicted)
• PSA: 160.83000
• Density: 1.55±0.1 g/cm3(Predicted)
• LogP: 1.33860
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

NLT 98% ^*data from raw suppliers

α-Etoposide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: α-Etoposide, s a cytotoxic agent (anticancer drug), which belongs to the drug type topoisomerase inhibitor. It is also an antineoplastic drug. α-Etoposide, is a cytotoxic agent (anticancer drug), which belongs to the drug type topoisomerase inhibitor. It is also an antineoplastic drug.

Technology Process of α-Etoposide

There total 8 articles about α-Etoposide 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:

C53H48N6O17 → etoposide (33419-42-0,89301-95-1,96554-38-0,96554-41-5,100007-53-2,100007-56-5,112246-48-7,112246-49-8,112246-50-1,132880-83-2,134623-79-3,136232-35-4,136232-37-6,136232-38-7,140223-11-6)

Guidance literature:

With palladium 10% on activated carbon; In 1,4-dioxane; methanol; at 30 ℃; for 4h; Inert atmosphere; Green chemistry;

Reference yield:

4,6-O-ethylidene-D-glucopyranose (18465-50-4,13224-97-0,13224-98-1,13224-99-2,13225-00-8,13225-01-9,13225-02-0,87068-63-1) → etoposide (33419-42-0,89301-95-1,96554-38-0,96554-41-5,100007-53-2,100007-56-5,112246-48-7,112246-49-8,112246-50-1,132880-83-2,134623-79-3,136232-35-4,136232-37-6,136232-38-7,140223-11-6)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / CH₂Cl₂ / 2 h / 0 °C

2: MeOH / CH₂Cl₂ / 20 h / 20 °C

3: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

4: BF₃*Et₂O / CH₂Cl₂ / 1) -20 deg C, 8 h, 2) -10 deg C, 30 min

5: MeOH, zinc acetate dihydrate / 1.5 h / Heating

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

DOI:10.1021/jo00067a071

Reference yield:

1-O-(trimethylsilyl)-4,6-O-ethylidene-2,3-di-O-(dichloroacetyl)-β-D-glucopyranose (149312-24-3) → etoposide (33419-42-0,89301-95-1,96554-38-0,96554-41-5,100007-53-2,100007-56-5,112246-48-7,112246-49-8,112246-50-1,132880-83-2,134623-79-3,136232-35-4,136232-37-6,136232-38-7,140223-11-6)

Guidance literature:

Multi-step reaction with 2 steps

1: BF₃*Et₂O / CH₂Cl₂ / 1) -20 deg C, 8 h, 2) -10 deg C, 30 min

2: MeOH, zinc acetate dihydrate / 1.5 h / Heating

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

DOI:10.1021/jo00067a071

upstream raw materials:

4,6-O-ethylidene-D-glucopyranose

1-O-(trimethylsilyl)-4,6-O-ethylidene-2,3-di-O-(dichloroacetyl)-β-D-glucopyranose

4,6-O-ethylidene-1,2,3-tri-O-(dichloroacetyl)-α-D-glucopyranose

etoposide

Refernces

• 1、 Allevi, Pietro,Anastasia, Mario,Ciuffreda, Pierangela,Bigatti, Ettore,Macdonald, Peter. "Stereoselective Glucosidation of Podophyllum Lignans. A New Simple Synthesis of Etoposide". . p. 4175 - 4178. Retrieved 2007/10/02.