methyl (1S,3S,4R,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxy-3-(trifluoroacetamido)cyclohexane-1-carboxylate

Base Information

• Chemical Name: methyl (1S,3S,4R,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxy-3-(trifluoroacetamido)cyclohexane-1-carboxylate
• CAS No.: 286956-25-0
• Molecular Formula: C₁₆H₂₁F₃N₂O₈
• Molecular Weight: 426.347

Synonyms:

Chemical Property of methyl (1S,3S,4R,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxy-3-(trifluoroacetamido)cyclohexane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,3S,4R,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxy-3-(trifluoroacetamido)cyclohexane-1-carboxylate

There total 11 articles about methyl (1S,3S,4R,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxy-3-(trifluoroacetamido)cyclohexane-1-carboxylate 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:

methyl (1S,3S,4S,5R)-1,5-di-O-acetyl-3-amino-1,4,5-trihydroxycyclohexane-1-carboxylate → methyl (1S,3S,4R,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxy-3-(trifluoroacetamido)cyclohexane-1-carboxylate (286956-25-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1 g / Et₃N; NaHCO₃ / 0.5 h

2: pyridine / CH₂Cl₂ / 0.33 h / -18 °C

3: 482 mg / tetrabutylammonium nitrite / acetonitrile / 0.5 h

4: pyridine / CH₂Cl₂ / 3.25 h / 0 - 20 °C

5: 327 mg / lithium azide / dimethylformamide / 0.75 h / 60 °C

6: H₂ / Pd/C / methanol / 0.5 h

7: 0.20 g / pyridine

With pyridine; lithium azide; hydrogen; sodium hydrogencarbonate; triethylamine; tetrabutylammonium nitrite; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Acylation / 2: Acylation / 3: Elimination / 4: Acylation / 5: Substitution / 6: Catalytic hydrogenation / 7: Acetylation;

DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

Reference yield:

(3aR,5R,7R,7aS)-5,7-Diacetoxy-2-oxo-hexahydro-2λ4-benzo[1,3,2]dioxathiole-5-carboxylic acid methyl ester → methyl (1S,3S,4R,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxy-3-(trifluoroacetamido)cyclohexane-1-carboxylate (286956-25-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 0.91 g / NaIO₄ / RuCl₃*H₂O / ethyl acetate; acetonitrile / 1 h / 0 - 20 °C

2: LiN₃ / dimethylformamide / 0.5 h / 80 °C

3: 561 mg / aq. H₂SO₄ / 0.5 h / 20 °C

4: H₂ / Pd/C / ethyl acetate / 2 h

5: 1 g / Et₃N; NaHCO₃ / 0.5 h

6: pyridine / CH₂Cl₂ / 0.33 h / -18 °C

7: 482 mg / tetrabutylammonium nitrite / acetonitrile / 0.5 h

8: pyridine / CH₂Cl₂ / 3.25 h / 0 - 20 °C

9: 327 mg / lithium azide / dimethylformamide / 0.75 h / 60 °C

10: H₂ / Pd/C / methanol / 0.5 h

11: 0.20 g / pyridine

With pyridine; sodium periodate; lithium azide; sulfuric acid; hydrogen; sodium hydrogencarbonate; triethylamine; tetrabutylammonium nitrite; ruthenium trichloride; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Oxidation / 2: Substitution / 3: Hydrolysis / 4: Catalytic hydrogenation / 5: Acylation / 6: Acylation / 7: Elimination / 8: Acylation / 9: Substitution / 10: Catalytic hydrogenation / 11: Acetylation;

DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

Reference yield:

methyl (1S,3S,4S,5R)-1,5-di-O-acetyl-3-azido-1,4,5-trihydroxycyclohexane-1-carboxylate (286956-17-0) → methyl (1S,3S,4R,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxy-3-(trifluoroacetamido)cyclohexane-1-carboxylate (286956-25-0)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂ / Pd/C / ethyl acetate / 2 h

2: 1 g / Et₃N; NaHCO₃ / 0.5 h

3: pyridine / CH₂Cl₂ / 0.33 h / -18 °C

4: 482 mg / tetrabutylammonium nitrite / acetonitrile / 0.5 h

5: pyridine / CH₂Cl₂ / 3.25 h / 0 - 20 °C

6: 327 mg / lithium azide / dimethylformamide / 0.75 h / 60 °C

7: H₂ / Pd/C / methanol / 0.5 h

8: 0.20 g / pyridine

With pyridine; lithium azide; hydrogen; sodium hydrogencarbonate; triethylamine; tetrabutylammonium nitrite; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Catalytic hydrogenation / 2: Acylation / 3: Acylation / 4: Elimination / 5: Acylation / 6: Substitution / 7: Catalytic hydrogenation / 8: Acetylation;

DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

upstream raw materials:

acetic anhydride

methyl 1,5-di-O-acetyl-3,4-O-sulfonylidenequinate

methyl (1S,3S,4S,5R)-1,5-di-O-acetyl-3-azido-1,4,5-trihydroxycyclohexane-1-carboxylate

methyl (1S,3S,4R,5R)-1,5-di-O-acetyl-1,4,5-trihydroxy-3-(trifluoroacetamido)cyclohexane-1-carboxylate

Downstream raw materials:

methyl (1S,3S,4R,5R)-4-acetamido-5-O-acetyl-1,5-dihydroxy-3-(trifluoroacetamido)cyclohexane-1-carboxylate

(1S,3R,4R,5S)-3-Acetoxy-4-acetylamino-1-(benzyloxy-diisopropylamino-phosphanyloxy)-5-(2,2,2-trifluoro-acetylamino)-cyclohexanecarboxylic acid methyl ester

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 286956-25-0 methyl (1S,3S,4R,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxy-3-(trifluoroacetamido)cyclohexane-1-carboxylate

Send

Send

Metric Ton KG G Pound L ML

Send

Send