3-phenylpropyl (3R^*,5R^*,7S^*)-3,5,7-trihydroxy-8-methylnonanoate

Base Information

• Chemical Name: 3-phenylpropyl (3R^*,5R^*,7S^*)-3,5,7-trihydroxy-8-methylnonanoate
• CAS No.: 113778-58-8
• Molecular Formula: C₁₉H₃₀O₅
• Molecular Weight: 338.444
• Mol file: 113778-58-8.mol

Synonyms:3-phenylpropyl (3R^*,5R^*,7S^*)-3,5,7-trihydroxy-8-methylnonanoate

Chemical Property of 3-phenylpropyl (3R^*,5R^*,7S^*)-3,5,7-trihydroxy-8-methylnonanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-phenylpropyl (3R^*,5R^*,7S^*)-3,5,7-trihydroxy-8-methylnonanoate

There total 6 articles about 3-phenylpropyl (3R^*,5R^*,7S^*)-3,5,7-trihydroxy-8-methylnonanoate 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: 79.0%

3-phenylpropyl (3R*,5R*,7S*)-5,7-bis(tert-butyldimethylsiloxy)-3-hydroxy-8-methylnonanoate (113830-25-4) → 3-phenylpropyl (3R*,5R*,7S*)-3,5,7-trihydroxy-8-methylnonanoate (113778-58-8)

Guidance literature:

With pyridine hydrogenfluoride; In acetonitrile; at 0 ℃; for 0.5h;

DOI:10.1021/ja00219a035

Reference yield: 50.0%

3-phenylpropyl 7-hydroxy-3,5-dioxo-8-methylnonanoate (113778-57-7) → (5S,7S)-5,7-Dihydroxy-8-methyl-3-oxo-nonanoic acid 3-phenyl-propyl ester (113778-83-9) + 3-phenylpropyl (3R*,5S*,7S*)-3,5,7-trihydroxy-8-methylnonanoate (113830-19-6) + 3-phenylpropyl (3S*,5R*,7S*)-3,5,7-trihydroxy-8-methylnonanoate (113830-18-5) + 3-phenylpropyl (3R*,5R*,7S*)-3,5,7-trihydroxy-8-methylnonanoate (113778-58-8)

Guidance literature:

With tetramethylammonium triacetoxyborohydride; In acetic acid; for 0.5h; Further byproducts given; Ambient temperature;

DOI:10.1021/ja00219a035

Reference yield:

3-Phenyl-1-propanol (122-97-4) → 3-phenylpropyl (3R*,5R*,7S*)-3,5,7-trihydroxy-8-methylnonanoate (113778-58-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / triethylamine / CH₂Cl₂ / 3.33 h / 40 °C

2: 35 percent / diisopropylamine, n-butyllithium / tetrahydrofuran; hexane / Ambient temperature

3: 55 percent / diisopropylamine, n-butyllithium / tetrahydrofuran; hexane / 0.02 h / -78 °C

4: 50 percent / tetramethylammonium triacetoxyborohydride / acetic acid / 0.5 h / Ambient temperature

With n-butyllithium; triethylamine; diisopropylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; hexane; dichloromethane; acetic acid;

DOI:10.1021/ja00219a035

upstream raw materials:

3-phenylpropyl 7-hydroxy-3,5-dioxo-8-methylnonanoate

3-phenylpropyl (3R^*,5R^*,7S^*)-5,7-bis(tert-butyldimethylsiloxy)-3-hydroxy-8-methylnonanoate

3-Phenyl-1-propanol

3-phenylpropyl-3-oxo butanoate

Downstream raw materials:

(3R^*,5R^*,7S^*)-3,7-bis(benzoyloxy)-5-hydroxy-8-methylnonanoic acid δ-lactone