3,5-bis(phenylethynyl)-4-(tert-butoxycarbonyl)-2-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-4H-[1,4]oxazine

Base Information

Chemical Name:3,5-bis(phenylethynyl)-4-(tert-butoxycarbonyl)-2-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-4H-[1,4]oxazine
CAS No.:943818-57-3
Molecular Formula:C₃₅H₃₃NO₇
Molecular Weight:579.65
Hs Code.:

Synonyms:3,5-bis(phenylethynyl)-4-(tert-butoxycarbonyl)-2-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-4H-[1,4]oxazine

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Chemical Property of 3,5-bis(phenylethynyl)-4-(tert-butoxycarbonyl)-2-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-4H-[1,4]oxazine

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Technology Process of 3,5-bis(phenylethynyl)-4-(tert-butoxycarbonyl)-2-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-4H-[1,4]oxazine

There total 3 articles about 3,5-bis(phenylethynyl)-4-(tert-butoxycarbonyl)-2-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-4H-[1,4]oxazine 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: 44.0%

: 943818-41-5
4-(tert-butoxycarbonyl)-3,5-bis(phenylethynyl)-4H-[1,4]oxazine

: 86-81-7
3,4,5-trimethoxy-benzaldehyde

: 943818-57-3
3,5-bis(phenylethynyl)-4-(tert-butoxycarbonyl)-2-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-4H-[1,4]oxazine

Guidance literature:: 4-(tert-butoxycarbonyl)-3,5-bis(phenylethynyl)-4H-[1,4]oxazine; With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.916667h;

3,4,5-trimethoxy-benzaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Further stages.;
DOI:10.1021/jo070528n

Reference yield:

: 943818-38-0
3,5-bis{[bis(phenyloxy)phosphoryl]oxy}-4-(tert-butoxycarbonyl)-[1,4]oxazine

: 943818-57-3
3,5-bis(phenylethynyl)-4-(tert-butoxycarbonyl)-2-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-4H-[1,4]oxazine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 91 percent / LiCl / Pd(PPh₃)4 / tetrahydrofuran / 2 h / Heating

2.1: n-butyllithium; HMPA / tetrahydrofuran; hexane / 0.92 h / -78 °C

2.2: 44 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; 1.1: Stille coupling;
DOI:10.1021/jo070528n

Reference yield:

: 943818-71-1
4-(tert-butoxycarbonyl)-morpholine-3,5-dione

: 943818-57-3
3,5-bis(phenylethynyl)-4-(tert-butoxycarbonyl)-2-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-4H-[1,4]oxazine

Guidance literature:: Multi-step reaction with 3 steps

1.1: 64 percent / KHMDS; HMPA / tetrahydrofuran / 0.33 h / -78 °C

2.1: 91 percent / LiCl / Pd(PPh₃)4 / tetrahydrofuran / 2 h / Heating

3.1: n-butyllithium; HMPA / tetrahydrofuran; hexane / 0.92 h / -78 °C

3.2: 44 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; potassium hexamethylsilazane; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; 2.1: Stille coupling;
DOI:10.1021/jo070528n