4β-(3-chloropropyl)sulfonamido-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin

Base Information

• Chemical Name: 4β-(3-chloropropyl)sulfonamido-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin
• CAS No.: 692755-50-3
• Molecular Formula: C₃₀H₄₀ClNO₉SSi
• Molecular Weight: 654.253

Synonyms:4β-(3-chloropropyl)sulfonamido-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin

Chemical Property of 4β-(3-chloropropyl)sulfonamido-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin

Chemical Property:

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Technology Process of 4β-(3-chloropropyl)sulfonamido-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin

There total 3 articles about 4β-(3-chloropropyl)sulfonamido-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin 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: 88.0%

3-chloro-n-propanesulfonyl chloride (1633-82-5) + 4-β-amino-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin (692755-45-6) → 4β-(3-chloropropyl)sulfonamido-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin (692755-50-3)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In dichloromethane; at 20 ℃; for 22h;

DOI:10.1021/jm031117b

Reference yield:

(5R,5aR,8aS,9S)-9-amino-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one (117507-84-3) → 4β-(3-chloropropyl)sulfonamido-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin (692755-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / imidazole / dimethylformamide / 17 h

2: 88 percent / DABCO / CH₂Cl₂ / 22 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm031117b

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 4β-(3-chloropropyl)sulfonamido-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin (692755-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / imidazole / dimethylformamide / 17 h

2: 88 percent / DABCO / CH₂Cl₂ / 22 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm031117b

upstream raw materials:

3-chloro-n-propanesulfonyl chloride

4-β-amino-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin

(5R,5aR,8aS,9S)-9-amino-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one

tert-butyldimethylsilyl chloride

Downstream raw materials:

3-Azido-propane-1-sulfonic acid [(5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-8-oxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-amide

4β-(3-azidopropyl)sulfonamido-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin

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