4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((6S,8S)-8-acetyl-5,8,10-trihydroxy-4,11-dioxo-4,6,7,8,9,11-hexahydro-anthra[2,3-b]thiophen-6-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-((6S,8S)-8-acetyl-5,8,10-trihydroxy-4,11-dioxo-4,6,7,8,9,11-hexahydro-anthra[2,3-b]thiophen-6-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester
• CAS No.: 76887-91-7
• Molecular Formula: C₃₃H₂₇F₃N₂O₁₃S
• Molecular Weight: 748.644
• Mol file: 76887-91-7.mol

Synonyms:

Chemical Property of 4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((6S,8S)-8-acetyl-5,8,10-trihydroxy-4,11-dioxo-4,6,7,8,9,11-hexahydro-anthra[2,3-b]thiophen-6-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,6S)-6-((6S,8S)-8-acetyl-5,8,10-trihydroxy-4,11-dioxo-4,6,7,8,9,11-hexahydro-anthra[2,3-b]thiophen-6-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

There total 21 articles about 4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((6S,8S)-8-acetyl-5,8,10-trihydroxy-4,11-dioxo-4,6,7,8,9,11-hexahydro-anthra[2,3-b]thiophen-6-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:

(+/-)-8-<1,1-(ethylenedioxy)ethyl>-5,8,10-trihydroxy-6,7,8,9-tetrahydroanthra<2,3-b>thiophene-4,11-dione (121715-72-8) → 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-((6S,8S)-8-acetyl-5,8,10-trihydroxy-4,11-dioxo-4,6,7,8,9,11-hexahydro-anthra[2,3-b]thiophen-6-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (76887-91-7,77026-60-9)

Guidance literature:

Multi-step reaction with 4 steps

1: Br₂, AIBN, H₂O / CHCl₃; CCl₄ / 2 h / 70 °C

2: CF₃CO₂H, H₂O / 1.5 h / 0 °C

3: 1.) benzeneboronic acid, CF₃CO₂H 2.) 2-methylpentane-2,4-diol, acetic acid / 1.) toluene, 0 deg C, 3 h, then RT 13 h 2.) CH₂Cl₂, acetone, RT, 2 h

4: Hg(CN)2, HgBr₂, moecular sieve 3 Aengstroem / CHCl₃ / 0.5 h / Ambient temperature

With 2-methyl-2,4-pentanediol; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; water; bromine; mercury(II) cyanide; acetic acid; trifluoroacetic acid; mercury dibromide; phenylboronic acid; In tetrachloromethane; chloroform;

DOI:10.1016/S0040-4039(00)96434-7

Reference yield:

(+/-)-8-acetyl-5,8,10-trihydroxy-2-trimethylsilyl-6,7,8,9-tetrahydroanthra<2,3-b>thiophene-4,11-dione (121715-70-6) → 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-((6S,8S)-8-acetyl-5,8,10-trihydroxy-4,11-dioxo-4,6,7,8,9,11-hexahydro-anthra[2,3-b]thiophen-6-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (76887-91-7,77026-60-9)

Guidance literature:

Multi-step reaction with 6 steps

1: p-TsOH / benzene / 3 h / Heating

2: n-Bu₄NF / tetrahydrofuran / 0.33 h / Ambient temperature

3: Br₂, AIBN, H₂O / CHCl₃; CCl₄ / 2 h / 70 °C

4: CF₃CO₂H, H₂O / 1.5 h / 0 °C

5: 1.) benzeneboronic acid, CF₃CO₂H 2.) 2-methylpentane-2,4-diol, acetic acid / 1.) toluene, 0 deg C, 3 h, then RT 13 h 2.) CH₂Cl₂, acetone, RT, 2 h

6: Hg(CN)2, HgBr₂, moecular sieve 3 Aengstroem / CHCl₃ / 0.5 h / Ambient temperature

With 2-methyl-2,4-pentanediol; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; tetrabutyl ammonium fluoride; water; bromine; mercury(II) cyanide; toluene-4-sulfonic acid; acetic acid; trifluoroacetic acid; mercury dibromide; phenylboronic acid; In tetrahydrofuran; tetrachloromethane; chloroform; benzene;

DOI:10.1016/S0040-4039(00)96434-7

Reference yield:

(+/-)-8-<1,1-(ethylenedioxy)ethyl>-5,8,10-trihydroxy-2-trimethylsilyl-6,7,8,9-tetrahydroanthra<2,3-b>thiophene-4,11-dione (121715-71-7) → 4-Nitro-benzoic acid (2S,3S,4S,6R)-6-((6S,8S)-8-acetyl-5,8,10-trihydroxy-4,11-dioxo-4,6,7,8,9,11-hexahydro-anthra[2,3-b]thiophen-6-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (76887-91-7,77026-60-9)

Guidance literature:

Multi-step reaction with 5 steps

1: n-Bu₄NF / tetrahydrofuran / 0.33 h / Ambient temperature

2: Br₂, AIBN, H₂O / CHCl₃; CCl₄ / 2 h / 70 °C

3: CF₃CO₂H, H₂O / 1.5 h / 0 °C

4: 1.) benzeneboronic acid, CF₃CO₂H 2.) 2-methylpentane-2,4-diol, acetic acid / 1.) toluene, 0 deg C, 3 h, then RT 13 h 2.) CH₂Cl₂, acetone, RT, 2 h

5: Hg(CN)2, HgBr₂, moecular sieve 3 Aengstroem / CHCl₃ / 0.5 h / Ambient temperature

With 2-methyl-2,4-pentanediol; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; tetrabutyl ammonium fluoride; water; bromine; mercury(II) cyanide; acetic acid; trifluoroacetic acid; mercury dibromide; phenylboronic acid; In tetrahydrofuran; tetrachloromethane; chloroform;

DOI:10.1016/S0040-4039(00)96434-7

upstream raw materials:

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

(6RS,8RS)-8-acetyl-5,6,8,10-tetrahydroxy-6,7,8,9-tetrahydroanthra<2,3-b>thiophene-4,11-dione

(+/-)-8-<1,1-(ethylenedioxy)ethyl>-5,8,10-trihydroxy-6,7,8,9-tetrahydroanthra<2,3-b>thiophene-4,11-dione

(+/-)-8-acetyl-5,8,10-trihydroxy-2-trimethylsilyl-6,7,8,9-tetrahydroanthra<2,3-b>thiophene-4,11-dione