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

Base Information

• Chemical Name: (3S^*,5R^*,7S^*)-3,7-bis(benzoyloxy)-5-hydroxy-8-methylnonanoic acid δ-lactone
• CAS No.: 113778-51-1
• Molecular Formula: C₂₄H₂₆O₆
• Molecular Weight: 410.467
• Mol file: 113778-51-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (3S^*,5R^*,7S^*)-3,7-bis(benzoyloxy)-5-hydroxy-8-methylnonanoic acid δ-lactone 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: 69.0%

benzoyl chloride (98-88-4) + (3S*,5R*,7S*)-3,5,7-trihydroxy-8-methylnonanoic acid δ-lactone (113778-50-0) → (3S*,5R*,7S*)-3,7-bis(benzoyloxy)-5-hydroxy-8-methylnonanoic acid δ-lactone (113778-51-1)

Guidance literature:

With pyridine; In dichloromethane; 0 deg C, 10 min. then room temp., 3.0 h.;

DOI:10.1021/ja00219a035

Reference yield:

3-phenylpropyl 6-methyl-3,5-dioxoheptanoate (109704-49-6) → (3S*,5R*,7S*)-3,7-bis(benzoyloxy)-5-hydroxy-8-methylnonanoic acid δ-lactone (113778-51-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 69 percent / tetramethylammonium triacetoxyborohydride / acetic acid / 5 h / Ambient temperature

2: 80 percent / triethylamine / CH₂Cl₂ / -10 deg C, 30 min. then room temp., 90 min.

3: 92 percent / diisobutylaluminium hydride / CH₂Cl₂ / 0.5 h / -78 °C

4: 32 percent / diisopropylamine, n-butyllithium / tetrahydrofuran; hexane / 0.02 h / -78 °C

5: 71 percent / pyridinium fluoride / acetonitrile / 0.5 h / 0 °C

6: 42 percent / 50percent HF / acetonitrile / 1 h

7: 69 percent / pyridine / CH₂Cl₂ / 0 deg C, 10 min. then room temp., 3.0 h.

With pyridine; n-butyllithium; hydrogen fluoride; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; diisopropylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; hexane; dichloromethane; acetic acid; acetonitrile;

DOI:10.1021/ja00219a035

Reference yield:

3-phenylpropyl (3S*,5S*)-3,5-dihydroxy-6-methylheptanoate (113778-36-2) → (3S*,5R*,7S*)-3,7-bis(benzoyloxy)-5-hydroxy-8-methylnonanoic acid δ-lactone (113778-51-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / triethylamine / CH₂Cl₂ / -10 deg C, 30 min. then room temp., 90 min.

2: 92 percent / diisobutylaluminium hydride / CH₂Cl₂ / 0.5 h / -78 °C

3: 32 percent / diisopropylamine, n-butyllithium / tetrahydrofuran; hexane / 0.02 h / -78 °C

4: 71 percent / pyridinium fluoride / acetonitrile / 0.5 h / 0 °C

5: 42 percent / 50percent HF / acetonitrile / 1 h

6: 69 percent / pyridine / CH₂Cl₂ / 0 deg C, 10 min. then room temp., 3.0 h.

With pyridine; n-butyllithium; hydrogen fluoride; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;

DOI:10.1021/ja00219a035

upstream raw materials:

benzoyl chloride

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

3-phenylpropyl 6-methyl-3,5-dioxoheptanoate

3-phenylpropyl (3S^*,5S^*)-3,5-dihydroxy-6-methylheptanoate