4-Nitro-benzoic acid (2S,3S,4S,6R)-6-[(1S,3S)-3,12-dihydroxy-10-methoxy-3-(2-methyl-[1,3]dioxolan-2-yl)-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,6R)-6-[(1S,3S)-3,12-dihydroxy-10-methoxy-3-(2-methyl-[1,3]dioxolan-2-yl)-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.: 115043-55-5
• Molecular Formula: C₃₈H₃₅F₃N₂O₁₄
• Molecular Weight: 800.696
• Mol file: 115043-55-5.mol

Synonyms:

Chemical Property of 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-[(1S,3S)-3,12-dihydroxy-10-methoxy-3-(2-methyl-[1,3]dioxolan-2-yl)-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):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-[(1S,3S)-3,12-dihydroxy-10-methoxy-3-(2-methyl-[1,3]dioxolan-2-yl)-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 2 articles about 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-[(1S,3S)-3,12-dihydroxy-10-methoxy-3-(2-methyl-[1,3]dioxolan-2-yl)-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:

2,3,6-trideoxy-1,4-di-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxopyranose (52583-22-9) + (+/-)-9-<1,1-(ethylenedioxy)ethyl>-cis-6,7,9-trihydroxy-4-methoxy-7,8,9,10-tetrahydronaphthacene-5,12-dione (115043-52-2,115043-53-3) → 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-[(1R,3R)-3,12-dihydroxy-10-methoxy-3-(2-methyl-[1,3]dioxolan-2-yl)-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 (115043-55-5,115114-89-1) + 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-[(1S,3S)-3,12-dihydroxy-10-methoxy-3-(2-methyl-[1,3]dioxolan-2-yl)-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 (115043-55-5,115114-89-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In diethyl ether; dichloromethane; at -15 ℃; for 4h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)96570-5

Reference yield:

2,3,6-trideoxy-1,4-di-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxopyranose (52583-22-9) + (+/-)-9-<1,1-(ethylenedioxy)ethyl>-cis-6,7,9-trihydroxy-4-methoxy-7,8,9,10-tetrahydronaphthacene-5,12-dione (115043-52-2,115043-53-3) → 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-[(1R,3R)-3,12-dihydroxy-10-methoxy-3-(2-methyl-[1,3]dioxolan-2-yl)-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 (115043-55-5,115114-89-1) + 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-[(1S,3S)-3,12-dihydroxy-10-methoxy-3-(2-methyl-[1,3]dioxolan-2-yl)-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 (115043-55-5,115114-89-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In diethyl ether; dichloromethane; at -15 ℃; for 4h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)96570-5

Reference yield: 53.0%

4-Nitro-benzoic acid (2S,3S,4S,6R)-6-[(1R,3R)-3,12-dihydroxy-10-methoxy-3-(2-methyl-[1,3]dioxolan-2-yl)-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 (115043-55-5,115114-89-1) → (-)-4'-O-p-nitrobenzoyl-3'-N-trifluoroacetyl-7,9-bis-epi-11-deoxydaunomycin (115043-56-6,120521-94-0)

Guidance literature:

With acetic acid; at 45 ℃; for 40h;

DOI:10.1016/S0040-4039(00)96570-5

upstream raw materials:

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

(+/-)-9-<1,1-(ethylenedioxy)ethyl>-cis-6,7,9-trihydroxy-4-methoxy-7,8,9,10-tetrahydronaphthacene-5,12-dione

Downstream raw materials:

(-)-4'-O-p-nitrobenzoyl-3'-N-trifluoroacetyl-7,9-bis-epi-11-deoxydaunomycin

(-)-4'-O-p-nitrobenzoyl-3'-N-trifluoroacetyl-11-deoxydaunomycin

11-deoxydaunomycin