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

Base Information

• Chemical Name: 3-phenylpropyl (3S^*,5S^*,7S^*)-5,7-bis(tert-butyldimethylsiloxy)-3-hydroxy-8-methylnonanoate
• CAS No.: 113830-22-1
• Molecular Formula: C₃₁H₅₈O₅Si₂
• Molecular Weight: 566.97

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

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

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

There total 1 articles about 3-phenylpropyl (3S^*,5S^*,7S^*)-5,7-bis(tert-butyldimethylsiloxy)-3-hydroxy-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: 43.0%

(3R*,5S*)-3,5-bis(tert-butyldimethylsiloxy)-6-methylheptanal (113778-63-5) + 3-phenylpropyl acetate (122-72-5) → 3-phenylpropyl (3R*,5S*,7S*)-5,7-bis(tert-butyldimethylsiloxy)-3-hydroxy-8-methylnonanoate (113830-21-0) + 3-phenylpropyl (3S*,5S*,7S*)-5,7-bis(tert-butyldimethylsiloxy)-3-hydroxy-8-methylnonanoate (113830-22-1)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.0166667h;

DOI:10.1021/ja00219a035

Reference yield: 64.0%

3-phenylpropyl (3S*,5S*,7S*)-5,7-bis(tert-butyldimethylsiloxy)-3-hydroxy-8-methylnonanoate (113830-22-1) → 3-phenylpropyl (3S*,5S*,7S*)-3,5,7-trihydroxy-8-methylnonanoate (113830-20-9)

Guidance literature:

With pyridine hydrogenfluoride; In acetonitrile; at 0 ℃; for 1.08333h;

DOI:10.1021/ja00219a035

Reference yield:

3-phenylpropyl (3S*,5S*,7S*)-5,7-bis(tert-butyldimethylsiloxy)-3-hydroxy-8-methylnonanoate (113830-22-1) → (3S*,5S*,7S*)-3,7-bis(benzoyloxy)-5-hydroxy-8-methylnonanoic acid δ-lactone (113778-55-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / pyridinium fluoride / acetonitrile / 1.08 h / 0 °C

2: 65 percent / 50percent HF / acetonitrile / 1 h

3: 85 percent / pyridine / CH₂Cl₂ / 0 deg C, 10 min. then room temp., 3.0 h.

With pyridine; hydrogen fluoride; pyridine hydrogenfluoride; In dichloromethane; acetonitrile;

DOI:10.1021/ja00219a035

upstream raw materials:

(3R^*,5S^*)-3,5-bis(tert-butyldimethylsiloxy)-6-methylheptanal

3-phenylpropyl acetate

Downstream raw materials:

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

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

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