meso-2-cyclohexene-1,4-diyl bis(diethyl phosphate)

Base Information

• Chemical Name: meso-2-cyclohexene-1,4-diyl bis(diethyl phosphate)
• CAS No.: 530128-88-2
• Molecular Formula: C₁₄H₂₈O₈P₂
• Molecular Weight: 386.319
• Mol file: 530128-88-2.mol

Synonyms:meso-2-cyclohexene-1,4-diyl bis(diethyl phosphate)

Chemical Property of meso-2-cyclohexene-1,4-diyl bis(diethyl phosphate)

Chemical Property:

Purity/Quality:

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Technology Process of meso-2-cyclohexene-1,4-diyl bis(diethyl phosphate)

There total 1 articles about meso-2-cyclohexene-1,4-diyl bis(diethyl phosphate) 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: 86.0%

(1S,4R)-Cyclohex-2-ene-1,4-diol (53762-85-9) + diethyl chlorophosphate (814-49-3) → meso-2-cyclohexene-1,4-diyl bis(diethyl phosphate) (530128-88-2)

Guidance literature:

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; at -40 - 0 ℃;

DOI:10.1021/ol035807l

Reference yield: 10.0%

diethylzinc (557-20-0) + meso-2-cyclohexene-1,4-diyl bis(diethyl phosphate) (530128-88-2) → (1R,2R)-phosphoric acid diethyl ester 2-ethyl-cyclohex-3-enyl ester + diethyl (1S,2S)-2-ethylcyclohex-3-enyl phosphate + (+/-)-(1R,2S)-phosphoric acid diethyl ester 2-ethyl-cyclohex-3-enyl ester

Guidance literature:

With copper(I) trifluoromethanesulfonate benzene; In toluene; at -40 ℃; for 16h; Title compound not separated from byproducts;

DOI:10.1021/ol035807l

Reference yield:

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) + meso-2-cyclohexene-1,4-diyl bis(diethyl phosphate) (530128-88-2) → (1R,2R)-2-allyl-3-cyclohexen-1-yl diethyl phosphate + (1S,2S)-2-allyl-3-cyclohexen-1-yl diethyl phosphate

Guidance literature:

With C₄₀H₄₅N₂O⁽¹⁺⁾*BF₄^(1-); potassium methanolate; copper(l) chloride; In tetrahydrofuran; at -20 ℃; for 48h; Overall yield = 52 %; Overall yield = 21.3 mg; enantioselective reaction; Sealed tube; Inert atmosphere;

DOI:10.1002/anie.201605125

upstream raw materials:

(1S,4R)-Cyclohex-2-ene-1,4-diol

diethyl chlorophosphate