(5S-(5alpha,5abeta,8aalpha,9beta))-5-(2-Chloro-4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro-9-((3-hydroxyphenyl)amino)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one

Base Information

• Chemical Name: (5S-(5alpha,5abeta,8aalpha,9beta))-5-(2-Chloro-4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro-9-((3-hydroxyphenyl)amino)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one
• CAS No.: 138261-35-5
• Molecular Formula: C₂₇H₂₄ClNO₈
• Molecular Weight: 525.942
• ChEMBL ID: CHEMBL169066
• Nikkaji Number: J467.415D
• Mol file: 138261-35-5.mol

Synonyms:(5S-(5alpha,5abeta,8aalpha,9beta))-5-(2-Chloro-4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro-9-((3-hydroxyphenyl)amino)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one;138261-35-5;Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5-(2-chloro-4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro-9-((3-hydroxyphenyl)amino)-, (5S-(5alpha,5abeta,8aalpha,9beta))-;CHEMBL169066

Chemical Property of (5S-(5alpha,5abeta,8aalpha,9beta))-5-(2-Chloro-4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro-9-((3-hydroxyphenyl)amino)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one

Chemical Property:

• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 525.1190444
• Heavy Atom Count: 37
• Complexity: 834

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C(=C(C(=C1)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)NC6=CC(=CC=C6)O)Cl)OC)O
• Isomeric SMILES: COC1=C(C(=C(C(=C1)[C@H]2[C@@H]3[C@H](COC3=O)[C@@H](C4=CC5=C(C=C24)OCO5)NC6=CC(=CC=C6)O)Cl)OC)O

Technology Process of (5S-(5alpha,5abeta,8aalpha,9beta))-5-(2-Chloro-4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro-9-((3-hydroxyphenyl)amino)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one

There total 4 articles about (5S-(5alpha,5abeta,8aalpha,9beta))-5-(2-Chloro-4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydro-9-((3-hydroxyphenyl)amino)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one 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:

4'-demethylepipodophyllotoxin (6559-91-7) → 4'-O-demethyl-2'-chloro-4β-(3-hydroxyanilino)-4-desoxypodophyllotoxin (138261-35-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / N-chlorosuccinimide (NCS) / dimethylformamide / 3.5 h / Ambient temperature

2: HBr (gas) / CH₂Cl₂ / 1 h / 0 °C

3: sodium iodide / acetone / 0.5 h / Ambient temperature

4: barium carbonate / 1,2-dichloro-ethane / Ambient temperature

With N-chloro-succinimide; hydrogen bromide; barium carbonate; sodium iodide; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00083a009

Reference yield:

4β-bromo-2'-chloro-4'-O-demethyl-4-desoxypodophyllotoxin (138261-32-2) → 4'-O-demethyl-2'-chloro-4β-(3-hydroxyanilino)-4-desoxypodophyllotoxin (138261-35-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium iodide / acetone / 0.5 h / Ambient temperature

2: barium carbonate / 1,2-dichloro-ethane / Ambient temperature

With barium carbonate; sodium iodide; In 1,2-dichloro-ethane; acetone;

DOI:10.1021/jm00083a009

Reference yield:

2'-chloro-4′-demethylepipodophyllotoxin (138261-31-1) → 4'-O-demethyl-2'-chloro-4β-(3-hydroxyanilino)-4-desoxypodophyllotoxin (138261-35-5)

Guidance literature:

Multi-step reaction with 3 steps

1: HBr (gas) / CH₂Cl₂ / 1 h / 0 °C

2: sodium iodide / acetone / 0.5 h / Ambient temperature

3: barium carbonate / 1,2-dichloro-ethane / Ambient temperature

With hydrogen bromide; barium carbonate; sodium iodide; In dichloromethane; 1,2-dichloro-ethane; acetone;

DOI:10.1021/jm00083a009

upstream raw materials:

m-Hydroxyaniline

4'-demethylepipodophyllotoxin

4β-bromo-2'-chloro-4'-O-demethyl-4-desoxypodophyllotoxin

2'-chloro-4′-demethylepipodophyllotoxin