4-Azido-N-[(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]-benzenesulfonamide

Base Information

• Chemical Name: 4-Azido-N-[(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]-benzenesulfonamide
• CAS No.: 692755-78-5
• Molecular Formula: C₂₇H₂₄N₄O₉S
• Molecular Weight: 580.575
• Mol file: 692755-78-5.mol

Synonyms:4-Azido-N-[(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]-benzenesulfonamide

Chemical Property of 4-Azido-N-[(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]-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Azido-N-[(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]-benzenesulfonamide

There total 3 articles about 4-Azido-N-[(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]-benzenesulfonamide 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: 92.0%

4β-(4-azidophenyl)sulfonamido-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin (692755-54-7) → 4-Azido-N-[(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]-benzenesulfonamide (692755-78-5)

Guidance literature:

With Dowex 50 x 20-200 ion-exchange resin; In methanol; for 16h;

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) → 4-Azido-N-[(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]-benzenesulfonamide (692755-78-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / imidazole / dimethylformamide / 17 h

2: 94 percent / DABCO / CH₂Cl₂ / 18 h / 20 °C

3: 92 percent / Dowex 50 x 20-200 ion-exchange resin / methanol / 16 h

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; Dowex 50 x 20-200 ion-exchange resin; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm031117b

Reference yield:

4-β-amino-4'-tert-butyldimethylsilyloxy-4'-O-demethyl-4-desoxypodophyllotoxin (692755-45-6) → 4-Azido-N-[(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]-benzenesulfonamide (692755-78-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / DABCO / CH₂Cl₂ / 18 h / 20 °C

2: 92 percent / Dowex 50 x 20-200 ion-exchange resin / methanol / 16 h

With 1,4-diaza-bicyclo[2.2.2]octane; Dowex 50 x 20-200 ion-exchange resin; In methanol; dichloromethane;

DOI:10.1021/jm031117b

upstream raw materials:

4β-(4-azidophenyl)sulfonamido-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

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