4''-(BENZYLOXYCARBONYL)-4''-DEMETHYLEPIPODOPHYLLOTOXIN

Base Information

• Chemical Name: 4''-(BENZYLOXYCARBONYL)-4''-DEMETHYLEPIPODOPHYLLOTOXIN
• CAS No.: 23363-33-9
• Molecular Formula: C29H26 O10
• Molecular Weight: 534.519
• Mol file: 23363-33-9.mol

Synonyms:Carbonicacid,4-(5,5a,6,8,8a,9-hexahydro-9-hydroxy-6-oxofuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-5-yl)-2,6-dimethoxyphenylphenylmethyl ester, [5R-(5a,5ab,8aa,9b)]-; Epipodophyllotoxin, 4'-demethyl-, 4'-(benzyl carbonate) (8CI);Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole, carbonic acid deriv.;4'-[(Benzyloxy)carbonyl]-4'-demethyl-4-epipodophyllotoxin

Chemical Property of 4''-(BENZYLOXYCARBONYL)-4''-DEMETHYLEPIPODOPHYLLOTOXIN

Chemical Property:

• PSA: 118.98000
• LogP: 4.11620

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4''-(BENZYLOXYCARBONYL)-4''-DEMETHYLEPIPODOPHYLLOTOXIN

There total 3 articles about 4''-(BENZYLOXYCARBONYL)-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: 97.0%

4'-demethylepipodophyllotoxin (6559-91-7) + benzyl chloroformate (501-53-1,94274-21-2) → 4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin (23363-33-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jm9800752

Reference yield:

podofilox (518-28-5) → 4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin (23363-33-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / TMSI / CH₂Cl₂ / 4.5 h / 0 °C

2: 97 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With trimethylsilyl iodide; triethylamine; In dichloromethane;

DOI:10.1021/jm9800752

Reference yield:

→ 4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin (23363-33-9)

Guidance literature:

DOI:10.1002/hlca.19690520411

upstream raw materials:

4'-demethylepipodophyllotoxin

benzyl chloroformate

podofilox

Downstream raw materials:

Carbonic acid benzyl ester 4-[(5R,5aR,8aR,9S)-9-(4-fluoro-phenoxy)-6-oxo-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

Carbonic acid benzyl ester 4-[(5R,5aR,8aR,9S)-9-(4-benzyloxy-phenoxy)-6-oxo-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

4-O-(3-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-4,6-O-ethylidene-β-D-glucopyranosyl)-4'-O-benzyloxycarbonyl-4'-O-demethyl-4-epipodophyllotoxin

4-O-(3-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-4,6-O-ethylidene-α-D-glucopyranosyl)-4'-O-benzyloxycarbonyl-4'-O-demethyl-4-epipodophyllotoxin

Refernces

• 1、 -. "ORGANOPLATINUM COMPOUNDS AND PHARMACEUTICAL COMPOSITION THEREOF AND METHOD OF PREPARING CRYSTAL OF hTop2". Paragraph 0023-0025; 0081-0082. . Retrieved 2020/10/21.
• 2、 -. "Preparation method of etoposide, teniposide and analogs of etoposide and teniposide". Paragraph 0100; 0101; 0102. . Retrieved 2017/01/02.