(S)-3-[(E)-3-((2R,4S,5R)-3,4-Dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclohexanone

Base Information

• Chemical Name: (S)-3-[(E)-3-((2R,4S,5R)-3,4-Dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclohexanone
• CAS No.: 109242-46-8
• Molecular Formula: C₁₉H₂₆NO₃P
• Molecular Weight: 347.394

Synonyms:(S)-3-[(E)-3-((2R,4S,5R)-3,4-Dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclohexanone

Chemical Property of (S)-3-[(E)-3-((2R,4S,5R)-3,4-Dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclohexanone

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Technology Process of (S)-3-[(E)-3-((2R,4S,5R)-3,4-Dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclohexanone

There total 2 articles about (S)-3-[(E)-3-((2R,4S,5R)-3,4-Dimethyl-2-oxo-5-phenyl-2λ⁵-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclohexanone 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: 82.0%

cyclohexenone (930-68-7) + (2R,4S,5R)-3,4-Dimethyl-5-phenyl-2-(prop-2-enyl)-2-oxo-1,3,2-oxazaphospholidine (109242-43-5) → (S)-3-[(E)-3-((2R,4S,5R)-3,4-Dimethyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclohexanone (109242-46-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1021/ja00250a047

Reference yield:

ephedrine (299-42-3,7009-81-6,90-83-5,6912-63-6) → (S)-3-[(E)-3-((2R,4S,5R)-3,4-Dimethyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclohexanone (109242-46-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / toluene / 1.) -40 deg C, 1 h, 2.) 25 deg C, 12 h

2: 82 percent / n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

With n-butyllithium; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1021/ja00250a047

Reference yield: 82.0%

(S)-3-[(E)-3-((2R,4S,5R)-3,4-Dimethyl-2-oxo-5-phenyl-2λ5-[1,3,2]oxazaphospholidin-2-yl)-allyl]-cyclohexanone (109242-46-8) → ((S)-3-Oxo-cyclohexyl)-acetaldehyde

Guidance literature:

With ozone; In dichloromethane; at -78 ℃;

DOI:10.1021/ja00250a047

upstream raw materials:

cyclohexenone

(2R,4S,5R)-3,4-Dimethyl-5-phenyl-2-(prop-2-enyl)-2-oxo-1,3,2-oxazaphospholidine

ephedrine

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