methyl (3R,4S,5R)-4-acetamido-5-acetoxy-3-aminocyclohex-1-ene-1-carboxylate

Base Information

• Chemical Name: methyl (3R,4S,5R)-4-acetamido-5-acetoxy-3-aminocyclohex-1-ene-1-carboxylate
• CAS No.: 352533-39-2
• Molecular Formula: C₁₂H₁₈N₂O₅
• Molecular Weight: 270.285
• Mol file: 352533-39-2.mol

Synonyms:methyl (3R,4S,5R)-4-acetamido-5-acetoxy-3-aminocyclohex-1-ene-1-carboxylate

Chemical Property of methyl (3R,4S,5R)-4-acetamido-5-acetoxy-3-aminocyclohex-1-ene-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3R,4S,5R)-4-acetamido-5-acetoxy-3-aminocyclohex-1-ene-1-carboxylate

There total 15 articles about methyl (3R,4S,5R)-4-acetamido-5-acetoxy-3-aminocyclohex-1-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: 70.0%

methyl (3R,4S,5R)-4-acetamido-5-acetoxy-3-azidocyclohex-1-ene-1-carboxylate (352533-37-0) → methyl (3R,4S,5R)-4-acetamido-5-acetoxy-3-aminocyclohex-1-ene-1-carboxylate (352533-39-2)

Guidance literature:

With hydrogen; Lindlar's catalyst; In ethanol; at 20 ℃; for 12h; under 757.561 Torr;

DOI:10.1016/S0008-6215(01)00079-9

Reference yield:

methyl 3,4-O-isopropylideneshikimate (88165-26-8) → methyl (3R,4S,5R)-4-acetamido-5-acetoxy-3-aminocyclohex-1-ene-1-carboxylate (352533-39-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 100 percent / pyridine / 1 h / 20 °C

2.1: 97 percent / SOCl₂; Et₃N / tetrahydrofuran / 3 h / 20 °C

3.1: 17 mg / pyridine / 1 h / 20 °C

4.1: 92 percent / NaN₃ / dimethylformamide / 20 h / 20 °C

5.1: 72 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

6.1: PPh₃ / tetrahydrofuran / 3 h / 20 °C

7.1: 106 mg / pyridine / CH₂Cl₂ / 1 h / 0 °C

8.1: 65 percent / NaH / tetrahydrofuran / 4 h / 20 °C

9.1: NaN₃; NH₄Cl / dimethylformamide / 20 h / 20 °C

9.2: 61 percent / Ac₂O / 2 h

10.1: 70 percent / H₂ / Lindlar catalyst / ethanol / 12 h / 20 °C / 757.56 Torr

With pyridine; thionyl chloride; sodium azide; hydrogen; sodium hydride; ammonium chloride; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(01)00079-9

Reference yield:

D-(-)-quinic acid (77-95-2) → methyl (3R,4S,5R)-4-acetamido-5-acetoxy-3-aminocyclohex-1-ene-1-carboxylate (352533-39-2)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 100 percent / H₂SO₄ / 20 °C

2.1: 47 percent / pyridine / 2 h / 20 °C

3.1: 61 percent / SOCl₂ / pyridine / 2 h / 20 °C

4.1: 92 percent / H₂SO₄ / methanol / 20 °C

5.1: 92 mg / Dowex-50 (H+) / acetone / 3 h / 20 °C

6.1: 100 percent / pyridine / 1 h / 20 °C

7.1: 97 percent / SOCl₂; Et₃N / tetrahydrofuran / 3 h / 20 °C

8.1: 17 mg / pyridine / 1 h / 20 °C

9.1: 92 percent / NaN₃ / dimethylformamide / 20 h / 20 °C

10.1: 72 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

11.1: PPh₃ / tetrahydrofuran / 3 h / 20 °C

12.1: 106 mg / pyridine / CH₂Cl₂ / 1 h / 0 °C

13.1: 65 percent / NaH / tetrahydrofuran / 4 h / 20 °C

14.1: NaN₃; NH₄Cl / dimethylformamide / 20 h / 20 °C

14.2: 61 percent / Ac₂O / 2 h

15.1: 70 percent / H₂ / Lindlar catalyst / ethanol / 12 h / 20 °C / 757.56 Torr

With pyridine; thionyl chloride; sodium azide; Dowex-50 (H+); sulfuric acid; hydrogen; sodium hydride; ammonium chloride; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0008-6215(01)00079-9

upstream raw materials:

methyl (3R,4S,5R)-4-acetamido-5-acetoxy-3-azidocyclohex-1-ene-1-carboxylate

methyl 3,4-O-isopropylideneshikimate

D-(-)-quinic acid

3,4,5-tri-O-acetyl quinate de methyle

Refernces