(2S,3S)-2-Benzyl-3-[(E)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-allyl]-2-methyl-cyclopentanone

Base Information

• Chemical Name: (2S,3S)-2-Benzyl-3-[(E)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-allyl]-2-methyl-cyclopentanone
• CAS No.: 150932-45-9
• Molecular Formula: C₂₄H₃₅N₂O₂P
• Molecular Weight: 414.528

Synonyms:(2S,3S)-2-Benzyl-3-[(E)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-allyl]-2-methyl-cyclopentanone

Chemical Property of (2S,3S)-2-Benzyl-3-[(E)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-allyl]-2-methyl-cyclopentanone

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Technology Process of (2S,3S)-2-Benzyl-3-[(E)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-allyl]-2-methyl-cyclopentanone

There total 3 articles about (2S,3S)-2-Benzyl-3-[(E)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-allyl]-2-methyl-cyclopentanone 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: 80.0%

2-methyl-2-cyclopenten-1-one (1120-73-6) + benzyl bromide (100-39-0) + (3aR,7aR)-2-allyloctahydro-1H-1,3-dimethyl-1,3,2-benzadiazaphosphole 2-oxide (146098-95-5) → (2S,3S)-2-Benzyl-3-[(E)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-allyl]-2-methyl-cyclopentanone (150932-45-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1021/jo000388g

Reference yield:

(R,R)-N,N'-dimethyl-1,2-diaminocyclohexane (68737-65-5) → (2S,3S)-2-Benzyl-3-[(E)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-allyl]-2-methyl-cyclopentanone (150932-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / Et₃N / benzene / 18 h / 20 °C

2: 80 percent / n-BuLi / hexane; tetrahydrofuran / -78 - 20 °C

With n-butyllithium; triethylamine; In tetrahydrofuran; hexane; benzene; 1: cyclocondensation / 2: Addition;

DOI:10.1021/jo000388g

Reference yield:

2-methyl-2-cyclopenten-1-one (1120-73-6) + benzyl bromide (100-39-0) + (3aR,7aR)-2-allyloctahydro-1H-1,3-dimethyl-1,3,2-benzadiazaphosphole 2-oxide (146098-95-5) → (2S,3S)-2-Benzyl-3-[(E)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-allyl]-2-methyl-cyclopentanone (150932-45-9) + (2R,3R)-2-Benzyl-3-[(E)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-allyl]-2-methyl-cyclopentanone

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, -78 deg C, 1 min then 0.5 h;

DOI:10.1021/jo00071a004

upstream raw materials:

2-methyl-2-cyclopenten-1-one

benzyl bromide

(3aR,7aR)-2-allyloctahydro-1H-1,3-dimethyl-1,3,2-benzadiazaphosphole 2-oxide

(R,R)-N,N'-dimethyl-1,2-diaminocyclohexane

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