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

Base Information

Chemical Name:methyl (1S,3S,4R,5R)-1,5-di-O-acetyl-1,4,5-trihydroxy-3-(trifluoroacetamido)cyclohexane-1-carboxylate
CAS No.:286956-21-6
Molecular Formula:C₁₄H₁₈F₃NO₈
Molecular Weight:385.294
Hs Code.:

Synonyms:

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

Chemical Property:

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

There total 7 articles about methyl (1S,3S,4R,5R)-1,5-di-O-acetyl-1,4,5-trihydroxy-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:

: (3aR,5R,7R,7aS)-5,7-Diacetoxy-2-oxo-hexahydro-2λ⁴-benzo[1,3,2]dioxathiole-5-carboxylic acid methyl ester

: 286956-21-6
methyl (1S,3S,4R,5R)-1,5-di-O-acetyl-1,4,5-trihydroxy-3-(trifluoroacetamido)cyclohexane-1-carboxylate

Guidance literature:: Multi-step reaction with 7 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

With pyridine; sodium periodate; lithium azide; sulfuric acid; hydrogen; sodium hydrogencarbonate; triethylamine; tetrabutylammonium nitrite; ruthenium trichloride; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Oxidation / 2: Substitution / 3: Hydrolysis / 4: Catalytic hydrogenation / 5: Acylation / 6: Acylation / 7: Elimination;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

Reference yield:

: 286956-13-6
methyl 1,5-di-O-acetyl-3,4-O-sulfonylidenequinate

: 286956-21-6
methyl (1S,3S,4R,5R)-1,5-di-O-acetyl-1,4,5-trihydroxy-3-(trifluoroacetamido)cyclohexane-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

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

2: 561 mg / aq. H₂SO₄ / 0.5 h / 20 °C

3: H₂ / Pd/C / ethyl acetate / 2 h

4: 1 g / Et₃N; NaHCO₃ / 0.5 h

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

6: 482 mg / tetrabutylammonium nitrite / acetonitrile / 0.5 h

With pyridine; lithium azide; sulfuric acid; hydrogen; sodium hydrogencarbonate; triethylamine; tetrabutylammonium nitrite; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: Hydrolysis / 3: Catalytic hydrogenation / 4: Acylation / 5: Acylation / 6: Elimination;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

Reference yield:

: 286956-17-0
methyl (1S,3S,4S,5R)-1,5-di-O-acetyl-3-azido-1,4,5-trihydroxycyclohexane-1-carboxylate

: 286956-21-6
methyl (1S,3S,4R,5R)-1,5-di-O-acetyl-1,4,5-trihydroxy-3-(trifluoroacetamido)cyclohexane-1-carboxylate

Guidance literature:: Multi-step reaction with 4 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

With pyridine; hydrogen; sodium hydrogencarbonate; triethylamine; tetrabutylammonium nitrite; palladium on activated charcoal; In dichloromethane; ethyl acetate; acetonitrile; 1: Catalytic hydrogenation / 2: Acylation / 3: Acylation / 4: Elimination;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8