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

Base Information

• Chemical Name: 4-Nitro-benzoic acid (2S,3R,4S,6R)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-6-((1S,3S)-3,5,12-trihydroxy-3-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 78499-71-5
• Molecular Formula: C₃₄H₂₉F₃N₂O₁₂
• Molecular Weight: 714.606

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

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

There total 2 articles about 4-Nitro-benzoic acid (2S,3R,4S,6R)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-6-((1S,3S)-3,5,12-trihydroxy-3-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-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: 53.0%

(S)-cis-1,2,3,4,6,11-hexahydro-1,3,5,12-tetrahydroxy-3-methylnaphthacene-6,11-quinone (78548-50-2) + 1-chloro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxohexopyranose (63700-25-4) → 4-Nitro-benzoic acid (2S,3S,4S,6R)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-6-((1S,3S)-3,5,12-trihydroxy-3-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-tetrahydro-pyran-3-yl ester (78499-71-5,81844-80-6)

Guidance literature:

With silver trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; at -5 ℃; for 3.5h;

DOI:10.1021/jm00171a010

Reference yield:

4-Nitro-benzoic acid (2S,3R,4S)-6-chloro-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (128572-89-4) + (S)-cis-1,2,3,4,6,11-hexahydro-1,3,5,12-tetrahydroxy-3-methylnaphthacene-6,11-quinone (78548-50-2) → 4-Nitro-benzoic acid (2S,3R,4S,6R)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-6-((1S,3S)-3,5,12-trihydroxy-3-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-tetrahydro-pyran-3-yl ester (78499-71-5,81844-80-6)

Guidance literature:

With silver trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; at -5 ℃; for 3.5h;

DOI:10.1021/jm00171a010

Reference yield:

4-Nitro-benzoic acid (2S,3S,4S,6R)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-6-((1S,3S)-3,5,12-trihydroxy-3-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-tetrahydro-pyran-3-yl ester (78499-71-5,81844-80-6) → (7S,9S)-7-<(3'-amino-2',3',6'-trideoxy-α-L-lyxohexopyranosyl)oxy>-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-methyl-5,12-naphthacenedione (81844-87-3,81844-88-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / 0.1 M aq. NaOH / CH₂Cl₂; methanol / 0.5 h / 0 °C

2: 0.1 M aq. NaOH / tetrahydrofuran / 1 h

With sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00171a010

upstream raw materials:

(S)-cis-1,2,3,4,6,11-hexahydro-1,3,5,12-tetrahydroxy-3-methylnaphthacene-6,11-quinone

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

4-Nitro-benzoic acid (2S,3R,4S)-6-chloro-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

Downstream raw materials:

(7S,9S)-7-<(3'-amino-2',3',6'-trideoxy-α-L-lyxohexopyranosyl)oxy>-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-methyl-5,12-naphthacenedione

(7S,9S)-7-<(3'-amino-2',3',6'-trideoxy-α-L-arabinohexapyranosyl)oxy>-7,8,9,10-tetrahydro-6,9,11-trihydroxy-9-methyl-5,12-naphthacenedione

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