4-Nitro-benzoic acid (2S,3R,4R,5S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-5-fluoro-4-iodo-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 4-Nitro-benzoic acid (2S,3R,4R,5S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-5-fluoro-4-iodo-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 211993-35-0
• Molecular Formula: C₃₄H₂₉FINO₁₃
• Molecular Weight: 805.506

Synonyms:

Chemical Property of 4-Nitro-benzoic acid (2S,3R,4R,5S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-5-fluoro-4-iodo-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Nitro-benzoic acid (2S,3R,4R,5S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-5-fluoro-4-iodo-2-methyl-tetrahydro-pyran-3-yl ester

There total 10 articles about 4-Nitro-benzoic acid (2S,3R,4R,5S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-5-fluoro-4-iodo-2-methyl-tetrahydro-pyran-3-yl ester 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: 62.0%

(+)-Daunomycinone (21794-55-8) + 2,3,6-trideoxy-2-fluoro-3-iodo-4-O-p-nitrobenzoyl-α-L-talopyranosyl bromide (211993-27-0) → 4-Nitro-benzoic acid (2S,3R,4R,5S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-5-fluoro-4-iodo-2-methyl-tetrahydro-pyran-3-yl ester (211993-35-0) + 4-Nitro-benzoic acid (2S,3R,4R,5S,6S)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-5-fluoro-4-iodo-2-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:

With 3 A molecular sieve; mercury dibromide; mercury(II) oxide; In dichloromethane; for 38h; Heating;

DOI:10.1016/S0008-6215(98)00026-3

Reference yield:

methyl 3-O-acetyl-4-O-benzyl-2,6-dideoxy-2-fluoro-α-L-idopyranoside (114643-57-1) → 4-Nitro-benzoic acid (2S,3R,4R,5S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-5-fluoro-4-iodo-2-methyl-tetrahydro-pyran-3-yl ester (211993-35-0)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂ / Pd black / dioxane; H₂O; acetic acid / 1 h / Ambient temperature

2: 97 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / Ambient temperature

3: 98 percent / Zemplen deacetylation / methanol

4: 94 percent / pyridine / CH₂Cl₂ / 1 h

5: NaI / dimethylformamide / 3 h / 90 °C

6: 4-dimethylaminopyridine / dimethylformamide / 2.5 h / Ambient temperature

7: 72 percent / H₂SO₄ / nitromethane / 2 h / Ambient temperature

8: 99 percent / 30percent HBr in AcOH / 2 h / Ambient temperature

9: 22 percent / yellow HgO, HgBr₂, molecular sieves 3A / CH₂Cl₂ / 38 h / Heating

With pyridine; dmap; 3 A molecular sieve; sulfuric acid; hydrogen bromide; hydrogen; pyridinium p-toluenesulfonate; sodium iodide; mercury dibromide; mercury(II) oxide; palladium; In 1,4-dioxane; methanol; nitromethane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00026-3

Reference yield:

4-nitro-benzoyl chloride (122-04-3) → 4-Nitro-benzoic acid (2S,3R,4R,5S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-5-fluoro-4-iodo-2-methyl-tetrahydro-pyran-3-yl ester (211993-35-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 4-dimethylaminopyridine / dimethylformamide / 2.5 h / Ambient temperature

2: 72 percent / H₂SO₄ / nitromethane / 2 h / Ambient temperature

3: 99 percent / 30percent HBr in AcOH / 2 h / Ambient temperature

4: 22 percent / yellow HgO, HgBr₂, molecular sieves 3A / CH₂Cl₂ / 38 h / Heating

With dmap; 3 A molecular sieve; sulfuric acid; hydrogen bromide; mercury dibromide; mercury(II) oxide; In nitromethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00026-3

upstream raw materials:

(+)-Daunomycinone

2,3,6-trideoxy-2-fluoro-3-iodo-4-O-p-nitrobenzoyl-α-L-talopyranosyl bromide

4-nitro-benzoyl chloride

methyl 3-O-acetyl-4-O-benzyl-2,6-dideoxy-2-fluoro-α-L-idopyranoside

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