4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1S,2R)-2-acetyl-2-hydroxy-4,11-dioxo-2,3,4,11-tetrahydro-1H-cyclopenta[b]anthracen-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-((1S,2R)-2-acetyl-2-hydroxy-4,11-dioxo-2,3,4,11-tetrahydro-1H-cyclopenta[b]anthracen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester
• CAS No.: 90364-55-9
• Molecular Formula: C₃₄H₂₇F₃N₂O₁₁
• Molecular Weight: 696.59
• Mol file: 90364-55-9.mol

Synonyms:

Chemical Property of 4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1S,2R)-2-acetyl-2-hydroxy-4,11-dioxo-2,3,4,11-tetrahydro-1H-cyclopenta[b]anthracen-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,6S)-6-((1S,2R)-2-acetyl-2-hydroxy-4,11-dioxo-2,3,4,11-tetrahydro-1H-cyclopenta[b]anthracen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

There total 24 articles about 4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1S,2R)-2-acetyl-2-hydroxy-4,11-dioxo-2,3,4,11-tetrahydro-1H-cyclopenta[b]anthracen-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:

cis-2-Acetyl-2,3-dihydro-2,3-dihydroxy-1H-cyclopentanthracene-4,11-dione (90269-95-7) + 1-chloro-2,3,6-trideoxy-4-O-(p-nitrobenzoyl)-3-(trifluoroacetamido)-α-L-lyxo-hexopyranose (78548-38-6) → 4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1R,2S)-2-acetyl-2-hydroxy-4,11-dioxo-2,3,4,11-tetrahydro-1H-cyclopenta[b]anthracen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (90270-00-1,90364-55-9) + 4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1S,2R)-2-acetyl-2-hydroxy-4,11-dioxo-2,3,4,11-tetrahydro-1H-cyclopenta[b]anthracen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (90270-00-1,90364-55-9)

Guidance literature:

With silver trifluoromethanesulfonate; calcium carbonate; In tetrahydrofuran; dichloromethane; at 25 ℃; for 0.25h; Yield given. Yields of byproduct given;

DOI:10.1021/jo00186a034

Reference yield:

cis-2-Acetyl-2,3-dihydro-2,3-dihydroxy-1H-cyclopentanthracene-4,11-dione (90269-95-7) + 1-chloro-2,3,6-trideoxy-4-O-(p-nitrobenzoyl)-3-(trifluoroacetamido)-α-L-lyxo-hexopyranose (78548-38-6) → 4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1R,2S)-2-acetyl-2-hydroxy-4,11-dioxo-2,3,4,11-tetrahydro-1H-cyclopenta[b]anthracen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (90270-00-1,90364-55-9) + 4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1S,2R)-2-acetyl-2-hydroxy-4,11-dioxo-2,3,4,11-tetrahydro-1H-cyclopenta[b]anthracen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (90270-00-1,90364-55-9)

Guidance literature:

With silver trifluoromethanesulfonate; calcium carbonate; In tetrahydrofuran; dichloromethane; at 25 ℃; for 0.25h; Yield given. Yields of byproduct given;

DOI:10.1021/jo00186a034

Reference yield:

5,8-Dihydro-6-methyl-1,4-naphthalenediol (90269-87-7) → 4-Nitro-benzoic acid (2S,3S,4S,6S)-6-((1R,2S)-2-acetyl-2-hydroxy-4,11-dioxo-2,3,4,11-tetrahydro-1H-cyclopenta[b]anthracen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (90270-00-1,90364-55-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 80 percent / KOH / butan-2-one / 15 h / Heating

2: 73 percent / potassium tert-butoxide / dimethylsulfoxide / 96 h / 60 °C

3: sodium metaperiodate, OsO₄ / dioxane; H₂O / 120 h / 25 °C

4: 33 percent / p-toluenesilfonic acid / toluene / 8 h / 80 °C

5: OsO₄ / dioxane; pyridine / 8 h / 25 °C

6: 56 percent / imidazole / dimethylformamide / 18 h / 25 °C

7: 74 percent / argentic oxide, 6 N nitric acid / dioxane / 10 °C

8: bis-(2-methoxy-ethyl) ether / 0.17 h / 140 °C

9: 23 percent / sodium acetate / acetic acid / 1 h / Heating

10: 67 percent / acetic acid, tetra-n-butylammonium fluoride / tetrahydrofuran / 18 h

11: silver trifluoromethanesulfonate, anhydrous CaCO₃ / CH₂Cl₂; tetrahydrofuran / 0.25 h / 25 °C

With 1H-imidazole; potassium hydroxide; sodium periodate; osmium(VIII) oxide; potassium tert-butylate; tetrabutyl ammonium fluoride; nitric acid; sodium acetate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; acetic acid; calcium carbonate; silver(l) oxide; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; diethylene glycol dimethyl ether; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; butanone;

DOI:10.1021/jo00186a034

upstream raw materials:

cis-2-Acetyl-2,3-dihydro-2,3-dihydroxy-1H-cyclopentanthracene-4,11-dione

1-chloro-2,3,6-trideoxy-4-O-(p-nitrobenzoyl)-3-(trifluoroacetamido)-α-L-lyxo-hexopyranose

5,8-Dihydro-6-methyl-1,4-naphthalenediol

1,2-Dihydro-5,8-dimethoxy-3-methylnaphthalene