methyl (1R,4S,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxycyclohex-2-ene-1-carboxylate

Base Information

Chemical Name:methyl (1R,4S,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxycyclohex-2-ene-1-carboxylate
CAS No.:286956-54-5
Molecular Formula:C₁₄H₁₉NO₇
Molecular Weight:313.307
Hs Code.:

Synonyms:methyl (1R,4S,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxycyclohex-2-ene-1-carboxylate

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Chemical Property of methyl (1R,4S,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxycyclohex-2-ene-1-carboxylate

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Technology Process of methyl (1R,4S,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxycyclohex-2-ene-1-carboxylate

There total 8 articles about methyl (1R,4S,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxycyclohex-2-ene-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: 24.0%

: 108-24-7
acetic anhydride

: 286956-51-2
methyl (1R,5R)-1,5-di-O-acetyl-1,5-dihydroxy-3-hydroxyliminocyclohex-2-ene-1-carboxylate

: 17012-22-5
methyl 4-acetamidobenzoate

: 286956-54-5
methyl (1R,4S,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxycyclohex-2-ene-1-carboxylate

Guidance literature:: With zinc; In acetic acid; at 20 ℃; for 48h;
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

: 286956-54-5
methyl (1R,4S,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxycyclohex-2-ene-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: DBU / tetrahydrofuran / 0.5 h / 70 °C

3: 1.35 g / aq. H₂SO₄ / tetrahydrofuran / 1 h / 20 °C

4: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

5: 0.55 g / LiN₃ / dimethylformamide / 1 h / 70 °C

6: dithiothreitol / pyridine; H₂O / 1 h / 20 °C

7: 340 mg / pyridine / 15 h / 20 °C

With pyridine; sodium periodate; lithium azide; sulfuric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diothiothreitol; ruthenium trichloride; In tetrahydrofuran; pyridine; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Oxidation / 2: Elimination / 3: Hydrolysis / 4: Acylation / 5: Substitution / 6: Reduction / 7: Acetylation;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8

Reference yield:

: 286956-49-8
methyl (1R,4R,5R)-1,5-di-O-acetyl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylate

: 286956-54-5
methyl (1R,4S,5R)-4-acetamido-1,5-di-O-acetyl-1,5-dihydroxycyclohex-2-ene-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

2: 0.55 g / LiN₃ / dimethylformamide / 1 h / 70 °C

3: dithiothreitol / pyridine; H₂O / 1 h / 20 °C

4: 340 mg / pyridine / 15 h / 20 °C

With pyridine; lithium azide; triethylamine; diothiothreitol; In pyridine; dichloromethane; water; N,N-dimethyl-formamide; 1: Acylation / 2: Substitution / 3: Reduction / 4: Acetylation;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1745::AID-EJOC1745>3.0.CO;2-8