(S)-1-O-[(2-cyanoethyloxy)(N,N-diisopropylamino)phosphanyl]-2-(4,4'-dimethoxytrityloxy)-1-(4-ethynylphenyl)ethanol

Base Information

Chemical Name:(S)-1-O-[(2-cyanoethyloxy)(N,N-diisopropylamino)phosphanyl]-2-(4,4'-dimethoxytrityloxy)-1-(4-ethynylphenyl)ethanol
CAS No.:1579992-46-3
Molecular Formula:C₄₀H₄₅N₂O₅P
Molecular Weight:664.781
Hs Code.:

Synonyms:(S)-1-O-[(2-cyanoethyloxy)(N,N-diisopropylamino)phosphanyl]-2-(4,4'-dimethoxytrityloxy)-1-(4-ethynylphenyl)ethanol

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Chemical Property of (S)-1-O-[(2-cyanoethyloxy)(N,N-diisopropylamino)phosphanyl]-2-(4,4'-dimethoxytrityloxy)-1-(4-ethynylphenyl)ethanol

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Technology Process of (S)-1-O-[(2-cyanoethyloxy)(N,N-diisopropylamino)phosphanyl]-2-(4,4'-dimethoxytrityloxy)-1-(4-ethynylphenyl)ethanol

There total 6 articles about (S)-1-O-[(2-cyanoethyloxy)(N,N-diisopropylamino)phosphanyl]-2-(4,4'-dimethoxytrityloxy)-1-(4-ethynylphenyl)ethanol 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: 79.0%

: 1579992-45-2
(S)-2-(4,4'-dimethoxytrityloxy)-1-(4-ethynylphenyl)ethanol

: 124482-92-4,89992-70-1
2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

: 1579992-46-3
(S)-1-O-[(2-cyanoethyloxy)(N,N-diisopropylamino)phosphanyl]-2-(4,4'-dimethoxytrityloxy)-1-(4-ethynylphenyl)ethanol

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 1.5h; Inert atmosphere;
DOI:10.1016/j.bmcl.2014.01.082

Reference yield:

: 13704-09-1
(S)-(-)-ethyl mandelate

: 1579992-46-3
(S)-1-O-[(2-cyanoethyloxy)(N,N-diisopropylamino)phosphanyl]-2-(4,4'-dimethoxytrityloxy)-1-(4-ethynylphenyl)ethanol

Guidance literature:: Multi-step reaction with 6 steps

1: iodine; silver trifluoromethanesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere; Darkness

2: sodium tetrahydroborate / ethanol / 1 h / 0 - 20 °C / Inert atmosphere

3: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; piperidine / 4 h / 20 °C / Inert atmosphere

4: potassium carbonate / water; methanol / 12 h / 20 °C / Inert atmosphere

5: pyridine / 2 h / 20 °C / Inert atmosphere

6: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

With piperidine; pyridine; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; copper(l) iodide; iodine; silver trifluoromethanesulfonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;
DOI:10.1016/j.bmcl.2014.01.082

Reference yield:

: (S)-(+)-1-(4-iodophenyl)-1,2-ethanediol

: 1579992-46-3
(S)-1-O-[(2-cyanoethyloxy)(N,N-diisopropylamino)phosphanyl]-2-(4,4'-dimethoxytrityloxy)-1-(4-ethynylphenyl)ethanol

Guidance literature:: Multi-step reaction with 4 steps

1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; piperidine / 4 h / 20 °C / Inert atmosphere

2: potassium carbonate / water; methanol / 12 h / 20 °C / Inert atmosphere

3: pyridine / 2 h / 20 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

With piperidine; pyridine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; water;
DOI:10.1016/j.bmcl.2014.01.082