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

Base Information

Chemical Name:3,5-bis-(phenylethynyl)-4-(tert-butoxycarbonyl)-2-[(tert-butyl-dimethyl-silanyloxy)-(3,4,5-trimethoxy-phenyl)-methyl]-4H-[1,4]oxazine
CAS No.:943818-75-5
Molecular Formula:C₄₁H₄₇NO₇Si
Molecular Weight:693.912
Hs Code.:

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

There total 4 articles about 3,5-bis-(phenylethynyl)-4-(tert-butoxycarbonyl)-2-[(tert-butyl-dimethyl-silanyloxy)-(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: 78.0%

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

: 18162-48-6
tert-butyldimethylsilyl chloride

: 943818-75-5
3,5-bis-(phenylethynyl)-4-(tert-butoxycarbonyl)-2-[(tert-butyl-dimethyl-silanyloxy)-(3,4,5-trimethoxy-phenyl)-methyl]-4H-[1,4]oxazine

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 50 ℃; for 14h;
DOI:10.1021/jo070528n

Reference yield:

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

: 943818-75-5
3,5-bis-(phenylethynyl)-4-(tert-butoxycarbonyl)-2-[(tert-butyl-dimethyl-silanyloxy)-(3,4,5-trimethoxy-phenyl)-methyl]-4H-[1,4]oxazine

Guidance literature:: Multi-step reaction with 3 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

3.1: 78 percent / imidazole / dimethylformamide / 14 h / 50 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1.1: Stille coupling;
DOI:10.1021/jo070528n

Reference yield:

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

: 943818-75-5
3,5-bis-(phenylethynyl)-4-(tert-butoxycarbonyl)-2-[(tert-butyl-dimethyl-silanyloxy)-(3,4,5-trimethoxy-phenyl)-methyl]-4H-[1,4]oxazine

Guidance literature:: Multi-step reaction with 4 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

4.1: 78 percent / imidazole / dimethylformamide / 14 h / 50 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; potassium hexamethylsilazane; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 2.1: Stille coupling;
DOI:10.1021/jo070528n