4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1R,3R)-3-acetyl-8-fluoro-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1R,3R)-3-acetyl-8-fluoro-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester
• CAS No.: 118173-16-3
• Molecular Formula: C₃₅H₂₈F₄N₂O₁₃
• Molecular Weight: 760.607

Synonyms:

Chemical Property of 4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1R,3R)-3-acetyl-8-fluoro-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1R,3R)-3-acetyl-8-fluoro-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

There total 22 articles about 4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1R,3R)-3-acetyl-8-fluoro-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-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: 39.0%

1-chloro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxohexopyranose (63700-25-4) + (+/-)-demethoxy-2-fluorodaunomycinone (118173-13-0) → 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-((1S,3S)-3-acetyl-8-fluoro-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (118173-16-3,118243-72-4) + 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-((1R,3R)-3-acetyl-8-fluoro-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (118173-16-3,118243-72-4)

Guidance literature:

With 3 A molecular sieve; mercury(II) cyanide; mercury dibromide; In tetrahydrofuran; dichloromethane; at 60 ℃; for 96h;

DOI:10.1016/S0040-4020(01)86162-7

Reference yield: 39.0%

1-chloro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxohexopyranose (63700-25-4) + (+/-)-demethoxy-2-fluorodaunomycinone (118173-13-0) → 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-((1S,3S)-3-acetyl-8-fluoro-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (118173-16-3,118243-72-4) + 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-((1R,3R)-3-acetyl-8-fluoro-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (118173-16-3,118243-72-4)

Guidance literature:

With 3 A molecular sieve; mercury(II) cyanide; mercury dibromide; In tetrahydrofuran; dichloromethane; at 60 ℃; for 96h;

DOI:10.1016/S0040-4020(01)86162-7

Reference yield:

5-amino-3H-isobenzofuran-1-one (65399-05-5) → 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-((1R,3R)-3-acetyl-8-fluoro-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (118173-16-3,118243-72-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) 40 percent aq. HPF₆, 2.) NaNO₂ / 1.) water, 0 deg C, 2.) water

2: 1,3,5-trimethyl-benzene / Heating

4: 1.) i-Pr₂NH, n-BuLi / 1.) THF, 2.) THF

5: 98 percent / BCl₃ / CH₂Cl₂ / 0.5 h / -78 °C

6: 1.) TMS-triflate, 4 Angstroem molecular sieve / 1.) CH₂Cl₂, ether, -42 deg C, then 0 deg C, 1 h, 2.) CH₂Cl₂, then -30 deg C, overnight

With hexafluorophosphoric acid; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trichloride; diisopropylamine; sodium nitrite; In dichloromethane; 1,3,5-trimethyl-benzene;

DOI:10.1016/S0040-4020(01)86162-7

upstream raw materials:

2,3,6-trideoxy-1,4-di-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxopyranose

(+/-)-demethoxy-2-fluorodaunomycinone

1-chloro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxohexopyranose

5-amino-3H-isobenzofuran-1-one

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