Acetoxycycloheximide

Base Information

• Chemical Name: Acetoxycycloheximide
• CAS No.: 2885-39-4
• Deprecated CAS: 11037-68-6,14172-67-9,3326-96-3
• Molecular Formula: C₁₇H₂₅NO₆
• Molecular Weight: 339.389
• UNII: UX3Y1I395S
• DSSTox Substance ID: DTXSID001028172
• Nikkaji Number: J22.559B
• Wikipedia: Acetoxycycloheximide
• Wikidata: Q17010821
• ChEMBL ID: CHEMBL509719
• Mol file: 2885-39-4.mol

Synonyms:acetoxycycloheximide;streptovitacin E-73

Chemical Property of Acetoxycycloheximide

Chemical Property:

• Vapor Pressure: 2.03E-13mmHg at 25°C
• Melting Point: 140°C
• Refractive Index: 1.5420 (estimate)
• Boiling Point: 529.4°Cat760mmHg
• Flash Point: 274°C
• PSA: 109.77000
• Density: 1.24g/cm³
• LogP: 1.05600
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 339.16818752
• Heavy Atom Count: 24
• Complexity: 543

Purity/Quality:

99% ^*data from raw suppliers

ACETOXYCYCLOHEXIMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(CC(C1=O)C(CC2CC(=O)NC(=O)C2)O)(C)OC(=O)C
• Isomeric SMILES: C[C@H]1C[C@@](C[C@H](C1=O)[C@@H](CC2CC(=O)NC(=O)C2)O)(C)OC(=O)C

Technology Process of Acetoxycycloheximide

There total 11 articles about Acetoxycycloheximide 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%

Acetic acid (1R,3S,5S)-3-[(R)-2-(2,6-dioxo-piperidin-4-yl)-1-triethylsilanyloxy-ethyl]-1,5-dimethyl-4-oxo-cyclohexyl ester (131057-04-0) → (+/-)-E-73 (2885-39-4,131102-35-7,14172-67-9,3326-96-3,11037-68-6)

Guidance literature:

With acetic acid; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1271/bbb1961.54.1531

Reference yield:

4-(tetrahydro-2H-pyran-2-yloxy)cyclohexanone (60739-53-9) → (+/-)-E-73 (2885-39-4,131102-35-7,14172-67-9,3326-96-3,11037-68-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 78 percent / diethyl ether / 1 h / Ambient temperature

2: 61 percent / pyridinium p-toluenesulfonate / ethanol / 4 h / 60 - 70 °C

3: 88 percent / pyridinium chlorochromate (PCC), NaOAc / CH₂Cl₂ / 8 h / Ambient temperature

4: 84 percent / dimethylformamide / 80 °C

5: 1) lithium diisopropylamide / 1) THF, -60 deg C, 20 min, 2) -60 to -5 deg C

6: 1) lithium diisopropylamide / 1) THF, -70 deg C, 15 min, 2) -70 deg C, 1 h

7: 30 percent aq. acetic acid / tetrahydrofuran / 3 h / Ambient temperature

8: 71 percent / triethylamine, 4-dimethylaminopyridine / 48 h / Ambient temperature

9: 40 percent / triethylamine, 4-dimethylaminopyridine / 7 h / ice-NaCl bath

10: 70 percent / aq. acetic acid / tetrahydrofuran / 4 h / Ambient temperature

With dmap; sodium acetate; pyridinium p-toluenesulfonate; acetic acid; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1271/bbb1961.54.1531

Reference yield:

1-methyl-1,4-cyclohexanediol (89794-52-5) → (+/-)-E-73 (2885-39-4,131102-35-7,14172-67-9,3326-96-3,11037-68-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 88 percent / pyridinium chlorochromate (PCC), NaOAc / CH₂Cl₂ / 8 h / Ambient temperature

2: 84 percent / dimethylformamide / 80 °C

3: 1) lithium diisopropylamide / 1) THF, -60 deg C, 20 min, 2) -60 to -5 deg C

4: 1) lithium diisopropylamide / 1) THF, -70 deg C, 15 min, 2) -70 deg C, 1 h

5: 30 percent aq. acetic acid / tetrahydrofuran / 3 h / Ambient temperature

6: 71 percent / triethylamine, 4-dimethylaminopyridine / 48 h / Ambient temperature

7: 40 percent / triethylamine, 4-dimethylaminopyridine / 7 h / ice-NaCl bath

8: 70 percent / aq. acetic acid / tetrahydrofuran / 4 h / Ambient temperature

With dmap; sodium acetate; acetic acid; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1271/bbb1961.54.1531

upstream raw materials:

Acetic acid (1R,3S,5S)-3-[(R)-2-(2,6-dioxo-piperidin-4-yl)-1-triethylsilanyloxy-ethyl]-1,5-dimethyl-4-oxo-cyclohexyl ester

4-(tetrahydro-2H-pyran-2-yloxy)cyclohexanone

1-methyl-1,4-cyclohexanediol

4-hydroxy-4-methylcyclohexanone

Refernces