(4S)-4-benzyl-3-[(4R,6R,8S)-4,6,8-trimethyl-9-(tetrahydro-2H-2-pyranyloxy)nonanoyl]-1,3-oxazolan-2-one

Base Information

• Chemical Name: (4S)-4-benzyl-3-[(4R,6R,8S)-4,6,8-trimethyl-9-(tetrahydro-2H-2-pyranyloxy)nonanoyl]-1,3-oxazolan-2-one
• CAS No.: 1437124-71-4
• Molecular Formula: C₂₇H₄₁NO₅
• Molecular Weight: 459.626

Synonyms:(4S)-4-benzyl-3-[(4R,6R,8S)-4,6,8-trimethyl-9-(tetrahydro-2H-2-pyranyloxy)nonanoyl]-1,3-oxazolan-2-one

Chemical Property of (4S)-4-benzyl-3-[(4R,6R,8S)-4,6,8-trimethyl-9-(tetrahydro-2H-2-pyranyloxy)nonanoyl]-1,3-oxazolan-2-one

Chemical Property:

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Technology Process of (4S)-4-benzyl-3-[(4R,6R,8S)-4,6,8-trimethyl-9-(tetrahydro-2H-2-pyranyloxy)nonanoyl]-1,3-oxazolan-2-one

There total 14 articles about (4S)-4-benzyl-3-[(4R,6R,8S)-4,6,8-trimethyl-9-(tetrahydro-2H-2-pyranyloxy)nonanoyl]-1,3-oxazolan-2-one 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: 93.0%

(S)-5-benzyloxazolidin-2-one (183072-04-0) + (4R,6R,8S)-4,6,8-trimethyl-9-(tetrahydro-2H-2-pyranyloxy)nonanoic acid (1437124-65-6) → (4S)-4-benzyl-3-[(4R,6R,8S)-4,6,8-trimethyl-9-(tetrahydro-2H-2-pyranyloxy)nonanoyl]-1,3-oxazolan-2-one (1437124-71-4)

Guidance literature:

With pivaloyl chloride; triethylamine; lithium chloride; In tetrahydrofuran; at -20 - 0 ℃; Inert atmosphere;

DOI:10.1039/c3ra22754e

Reference yield:

tert-butyl(dimethyl)[(2S,4S,6S)-2,4,6-trimethyl-7-(tetrahydro-2H-2-pyranyloxy)heptyl]oxysilane (1437124-48-5) → (4S)-4-benzyl-3-[(4R,6R,8S)-4,6,8-trimethyl-9-(tetrahydro-2H-2-pyranyloxy)nonanoyl]-1,3-oxazolan-2-one (1437124-71-4)

Guidance literature:

Multi-step reaction with 6 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 25 °C / Inert atmosphere

2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; dichloromethane / 3 h / 25 °C / Inert atmosphere

3: dichloromethane / 12 h / 25 °C / Inert atmosphere

4: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 0 - 25 °C / Inert atmosphere

5: lithium hydroxide monohydrate / water; methanol / 0 - 25 °C / Inert atmosphere

6: triethylamine; pivaloyl chloride; lithium chloride / tetrahydrofuran / -20 - 0 °C / Inert atmosphere

With sodium tetrahydroborate; nickel(II) chloride hexahydrate; lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; pivaloyl chloride; triethylamine; lithium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; 3: |Wittig Olefination;

DOI:10.1039/c3ra22754e

Reference yield:

ethyl (E,4S,6R,8S)-4,6,8-trimethyl-9-(tetrahydro-2H-2-pyranyloxy)-2-nonenoate (1437123-98-2) → (4S)-4-benzyl-3-[(4R,6R,8S)-4,6,8-trimethyl-9-(tetrahydro-2H-2-pyranyloxy)nonanoyl]-1,3-oxazolan-2-one (1437124-71-4)

Guidance literature:

Multi-step reaction with 3 steps

1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 0 - 25 °C / Inert atmosphere

2: lithium hydroxide monohydrate / water; methanol / 0 - 25 °C / Inert atmosphere

3: triethylamine; pivaloyl chloride; lithium chloride / tetrahydrofuran / -20 - 0 °C / Inert atmosphere

With sodium tetrahydroborate; nickel(II) chloride hexahydrate; lithium hydroxide monohydrate; pivaloyl chloride; triethylamine; lithium chloride; In tetrahydrofuran; methanol; water;

DOI:10.1039/c3ra22754e

upstream raw materials:

tert-butyl(dimethyl)[(2S,4S,6S)-2,4,6-trimethyl-7-(tetrahydro-2H-2-pyranyloxy)heptyl]oxysilane

(2S,4R,6S)-2,4,6-trimethyl-7-(tetrahydro-2H-2-pyranyloxy)-heptan-1-ol

ethyl (E,4S,6R,8S)-4,6,8-trimethyl-9-(tetrahydro-2H-2-pyranyloxy)-2-nonenoate

ethyl (4R,6R,8S)-4,6,8-trimethyl-9-(tetrahydro-2H-2-pyranyloxy)nonanoate

Downstream raw materials:

(4S)-4-benzyl-3-[(2S,4S,6R,8S)-2,4,6,8-tetramethyl-9-(tetrahydro-2H-2-pyranyloxy)nonanoyl]-1,3-oxazolan-2-one

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