N-{(2R,4aR,6R,7R,8R,8aS)-6-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-2-fluoro-5-nitro-benzamide

Base Information

• Chemical Name: N-{(2R,4aR,6R,7R,8R,8aS)-6-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-2-fluoro-5-nitro-benzamide
• CAS No.: 660438-57-3
• Molecular Formula: C₃₆H₃₂FN₃O₁₀S
• Molecular Weight: 717.729
• Mol file: 660438-57-3.mol

Synonyms:N-{(2R,4aR,6R,7R,8R,8aS)-6-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-2-fluoro-5-nitro-benzamide

Chemical Property of N-{(2R,4aR,6R,7R,8R,8aS)-6-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-2-fluoro-5-nitro-benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{(2R,4aR,6R,7R,8R,8aS)-6-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-2-fluoro-5-nitro-benzamide

There total 4 articles about N-{(2R,4aR,6R,7R,8R,8aS)-6-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-2-fluoro-5-nitro-benzamide 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: 75.0%

2-fluoro-5-nitrobenzoic acid (7304-32-7) + (2R,4aR,6R,7R,8R,8aS)-7-Amino-6-[2-(1-benzenesulfonyl-1H-indol-3-yl)-ethoxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (660438-55-1) → N-{(2R,4aR,6R,7R,8R,8aS)-6-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-2-fluoro-5-nitro-benzamide (660438-57-3)

Guidance literature:

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo0352068

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → N-{(2R,4aR,6R,7R,8R,8aS)-6-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-2-fluoro-5-nitro-benzamide (660438-57-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / pyridinium p-toluenesulfonate / dimethylformamide / 2 h / 85 °C

2: K₂CO₃ / methanol

3: 75 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / CH₂Cl₂ / 0 - 20 °C

With pyridinium p-toluenesulfonate; potassium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0352068

Reference yield:

N-{(2R,3R,4R,5S,6R)-2-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-2,2,2-trifluoro-acetamide → N-{(2R,4aR,6R,7R,8R,8aS)-6-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-2-fluoro-5-nitro-benzamide (660438-57-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / pyridinium p-toluenesulfonate / dimethylformamide / 2 h / 85 °C

2: K₂CO₃ / methanol

3: 75 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / CH₂Cl₂ / 0 - 20 °C

With pyridinium p-toluenesulfonate; potassium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0352068

upstream raw materials:

2-fluoro-5-nitrobenzoic acid

(2R,4aR,6R,7R,8R,8aS)-7-Amino-6-[2-(1-benzenesulfonyl-1H-indol-3-yl)-ethoxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

benzaldehyde dimethyl acetal

N-{(2R,4aR,6R,7R,8R,8aS)-6-[2-(1-Benzenesulfonyl-1H-indol-3-yl)-ethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-2,2,2-trifluoro-acetamide