N-cyclohexyl (1S,4R,5R)-1-hydroxy-4,5-O-isopropylidene-3-oxo-cyclohexane-1-carboxamide

Base Information

• Chemical Name: N-cyclohexyl (1S,4R,5R)-1-hydroxy-4,5-O-isopropylidene-3-oxo-cyclohexane-1-carboxamide
• CAS No.: 681215-46-3
• Molecular Formula: C₁₆H₂₅NO₅
• Molecular Weight: 311.378
• Mol file: 681215-46-3.mol

Synonyms:N-cyclohexyl (1S,4R,5R)-1-hydroxy-4,5-O-isopropylidene-3-oxo-cyclohexane-1-carboxamide

Chemical Property of N-cyclohexyl (1S,4R,5R)-1-hydroxy-4,5-O-isopropylidene-3-oxo-cyclohexane-1-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-cyclohexyl (1S,4R,5R)-1-hydroxy-4,5-O-isopropylidene-3-oxo-cyclohexane-1-carboxamide

There total 3 articles about N-cyclohexyl (1S,4R,5R)-1-hydroxy-4,5-O-isopropylidene-3-oxo-cyclohexane-1-carboxamide 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: 81.0%

N-cyclohexyl 4,5-O-isopropylidene quinamide (874473-01-5) → N-cyclohexyl (1S,4R,5R)-1-hydroxy-4,5-O-isopropylidene-3-oxo-cyclohexane-1-carboxamide (681215-46-3)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.carres.2003.10.026

Reference yield:

(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone (32384-42-2) → N-cyclohexyl (1S,4R,5R)-1-hydroxy-4,5-O-isopropylidene-3-oxo-cyclohexane-1-carboxamide (681215-46-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / 0.33 h / microwave irradiation

2: 81 percent / pyridinium chlorochromate; 4A MS / CH₂Cl₂ / 3 h / 20 °C

With pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/j.carres.2003.10.026

Reference yield:

D-(-)-quinic acid (77-95-2) → N-cyclohexyl (1S,4R,5R)-1-hydroxy-4,5-O-isopropylidene-3-oxo-cyclohexane-1-carboxamide (681215-46-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / Na₂SO₄; H₂SO₄ / 1 h / Heating

2: 97 percent / 0.33 h / microwave irradiation

3: 81 percent / pyridinium chlorochromate; 4A MS / CH₂Cl₂ / 3 h / 20 °C

With sulfuric acid; sodium sulfate; pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/j.carres.2003.10.026

upstream raw materials:

N-cyclohexyl 4,5-O-isopropylidene quinamide

(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

D-(-)-quinic acid

Downstream raw materials:

N-cyclohexyl (4R,5R)-4,5-O-isopropylidene-3-oxo-1-cyclohexene-1-carboxamide

N-cyclohexyl (3S,4S,5R)-3-hydroxy-4,5-O-isopropylidene-1-cyclohexene-1-carboxamide