Valilactone

Base Information

• Chemical Name: Valilactone
• CAS No.: 113276-96-3
• Molecular Formula: C₂₂H₃₉NO₅
• Molecular Weight: 397.555
• DSSTox Substance ID: DTXSID80921027
• Wikidata: Q82893755
• Metabolomics Workbench ID: 98467
• ChEMBL ID: CHEMBL492253
• Mol file: 113276-96-3.mol

Synonyms:5-(N-formyl-L-valinyloxy)-2-hexyl-3-hydroxydecanoic lactone;valilactone

Chemical Property of Valilactone

Chemical Property:

• Vapor Pressure: 8.44E-12mmHg at 25°C
• Boiling Point: 541.7°Cat760mmHg
• Flash Point: 281.4°C
• PSA: 81.70000
• Density: 1.014g/cm³
• LogP: 5.17800
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 16
• Exact Mass: 397.28282334
• Heavy Atom Count: 28
• Complexity: 480

Purity/Quality:

≥98% ^*data from raw suppliers

Valilactone ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC1C(OC1=O)CC(CCCCC)OC(=O)C(C(C)C)NC=O
• Isomeric SMILES: CCCCCC[C@H]1[C@@H](OC1=O)C[C@H](CCCCC)OC(=O)[C@H](C(C)C)NC=O

Technology Process of Valilactone

There total 28 articles about Valilactone 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: 99.0%

2-formylamino-3-methyl-butyric acid (2S,2R,3S,4S)-1-(3-hexyl-4-oxo-oxetan-2-ylmethyl)-hex-4-enyl ester → valilactone (113276-96-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; at 20 ℃; for 12h; under 760 Torr;

DOI:10.1021/ol061651o

Reference yield: 88.0%

(3S,4S,2'S)-3-hexyl-4-(2'-hydroxyhept-1'-yl)oxetan-2-one (902135-60-8) + N-formyl-L-valine (4289-97-8) → valilactone (113276-96-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 21h;

DOI:10.1021/jo060844m

Reference yield:

1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-octan-1-one (907217-45-2) → valilactone (113276-96-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 78 percent / TMEDA / CH₂Cl₂ / 2 h / 0 °C

2: 75 percent / DMAP / CH₂Cl₂ / 46 h / 20 °C

3: 87 percent / NaHCO₃; I₂ / acetone; H₂O / 15 h / 0 °C

4: 97 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 3 h / -15 °C

5: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

6: 87 percent / NEt₃ / CH₂Cl₂ / 3 h / 0 °C

7: 94 percent / H₂ / Pd(OH)2 / methanol / 7 h / 20 °C

8: 71 percent / K₂CO₃ / tetrahydrofuran / 12 h / 20 °C

9: 92 percent / HF*Py / tetrahydrofuran / 14 h / 20 °C

10: 88 percent / DCC; DMAP / CH₂Cl₂ / 21 h / 20 °C

With 2,6-dimethylpyridine; dmap; N,N,N,N,-tetramethylethylenediamine; hydrogen; iodine; sodium hydrogencarbonate; potassium carbonate; pyridine hydrogenfluoride; triethylamine; dicyclohexyl-carbodiimide; tetramethylammonium triacetoxyborohydride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; acetone; acetonitrile;

DOI:10.1021/jo060844m

upstream raw materials:

<1S<1S<3S(E),4S>>>-benzyl 1-<1-<(3-hex-1-enyl-1-2-oxo-4-oxetanyl),ethyl hexyloxycarbonyl>21-methylpropylcarbamate>

formyl acetic anhydride

(3S,4S,2'S)-3-hexyl-4-(2'-hydroxyhept-1'-yl)oxetan-2-one

N-formyl-L-valine