diethyl (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(thien-2-yl)prop-1-enylphosphonate

Base Information

Chemical Name:diethyl (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(thien-2-yl)prop-1-enylphosphonate
CAS No.:939387-94-7
Molecular Formula:C₂₀H₂₆NO₅PS
Molecular Weight:423.47
Hs Code.:

Synonyms:diethyl (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(thien-2-yl)prop-1-enylphosphonate

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Chemical Property of diethyl (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(thien-2-yl)prop-1-enylphosphonate

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Technology Process of diethyl (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(thien-2-yl)prop-1-enylphosphonate

There total 6 articles about diethyl (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(thien-2-yl)prop-1-enylphosphonate 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: 77.0%

: 939387-94-7
diethyl (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(thien-2-yl)prop-1-enylphosphonate

Guidance literature:

Reference yield:

: 939387-56-1
diethyl 3-[N-benzyloxy-N-(2-nitrobenzenesulfonyl)amino]prop-1-ynylphosphonate

: 939387-94-7
diethyl (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(thien-2-yl)prop-1-enylphosphonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: Bu₃SnH / Pd(PPh₃)4 / tetrahydrofuran / 3 h / 0 - 20 °C

1.2: (2-furyl)3P; CuI / Pd₂dba3*CHCl₃ / 1-methyl-pyrrolidin-2-one / 20 °C

2.1: K₂CO₃; DMSO; PhSH / acetonitrile / 70 °C

2.2: acetonitrile

With tri-n-butyl-tin hydride; potassium carbonate; dimethyl sulfoxide; thiophenol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; acetonitrile; 1.2: Stille coupling;
DOI:10.1021/jo0700981

Reference yield:

: diethyl (3-(tetrahydro-2H-pyran-2-yl)oxy)prop-1-yn-1-ylphosphonate

: 939387-94-7
diethyl (Z)-3-[N-acetyl-N-(benzyloxy)amino]-1-(thien-2-yl)prop-1-enylphosphonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 8.75 g / p-TsOH / methanol / 20 °C

2.1: 71 percent / DEAD; PPh₃ / tetrahydrofuran / 20 h / 20 °C

3.1: Bu₃SnH / Pd(PPh₃)4 / tetrahydrofuran / 3 h / 0 - 20 °C

3.2: (2-furyl)3P; CuI / Pd₂dba3*CHCl₃ / 1-methyl-pyrrolidin-2-one / 20 °C

4.1: K₂CO₃; DMSO; PhSH / acetonitrile / 70 °C

4.2: acetonitrile

With tri-n-butyl-tin hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; thiophenol; triphenylphosphine; diethylazodicarboxylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; acetonitrile; 2.1: Mitsunobu coupling / 3.2: Stille coupling;
DOI:10.1021/jo0700981