Imidazo[1,2-a]pyridine, 8-azido-5,6,7,8-tetrahydro-2-(2-phenylethynyl)-6,7-bis(phenylmethoxy)-5 -[(phenylmethoxy)methyl]-, (5R,6R,7R,8S)-

Base Information

Chemical Name:Imidazo[1,2-a]pyridine, 8-azido-5,6,7,8-tetrahydro-2-(2-phenylethynyl)-6,7-bis(phenylmethoxy)-5 -[(phenylmethoxy)methyl]-, (5R,6R,7R,8S)-
CAS No.:922163-77-7
Molecular Formula:C37H33N5O3
Molecular Weight:595.701
Hs Code.:

Synonyms:

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Chemical Property of Imidazo[1,2-a]pyridine, 8-azido-5,6,7,8-tetrahydro-2-(2-phenylethynyl)-6,7-bis(phenylmethoxy)-5 -[(phenylmethoxy)methyl]-, (5R,6R,7R,8S)-

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MSDS Files:: SDS file from LookChem

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Technology Process of Imidazo[1,2-a]pyridine, 8-azido-5,6,7,8-tetrahydro-2-(2-phenylethynyl)-6,7-bis(phenylmethoxy)-5 -[(phenylmethoxy)methyl]-, (5R,6R,7R,8S)-

There total 16 articles about Imidazo[1,2-a]pyridine, 8-azido-5,6,7,8-tetrahydro-2-(2-phenylethynyl)-6,7-bis(phenylmethoxy)-5 -[(phenylmethoxy)methyl]-, (5R,6R,7R,8S)- 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: 92.0%

: 922163-76-6
(5R,6R,7R,8R)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-ol

: 922163-77-7
(5R,6R,7R,8S)-8-Azido-6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine

Guidance literature:: With diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 20 ℃; for 4h;
DOI:10.1021/ja066743n

Reference yield:

: 922163-66-4
(2S,3S,4S)-2,3,5-Tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-pentanal

: 922163-77-7
(5R,6R,7R,8S)-8-Azido-6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine

Guidance literature:: Multi-step reaction with 12 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -20 - 20 °C

1.2: tetrahydrofuran / 1 h / -78 - 20 °C

2.1: trifluoroacetic acid / CHCl₃ / 0.42 h / 20 °C

3.1: 0.86 g / 4-N,N-dimethylaminopyridine; pyridine / 0.5 h / 20 °C

4.1: 90 percent / N-iodosuccinimide / acetonitrile / 12 h / 20 °C

5.1: 96 percent / aq. HCl / dioxane / 2 h / 20 °C

6.1: 89 percent / trifluoromethanesulfonic anhydride; pyridine / CH₂Cl₂ / -15 - 50 °C

7.1: sodium methoxide / CH₂Cl₂ / 0.17 h / 20 °C

8.1: 0.822 g / diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 - 20 °C

9.1: 93 percent / EtMgBr / tetrahydrofuran / 0.17 h / 0 °C

10.1: 96 percent / Et₃N; CuI; Pd(PPh₃)4 / dimethylformamide / 16 h / 80 °C

11.1: 76 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

12.1: 92 percent / diphenylphosphoryl azide; DBU / toluene / 4 h / 20 °C

With pyridine; hydrogenchloride; dmap; N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; diphenylphosphoranyl azide; ethylmagnesium bromide; tetrabutyl ammonium fluoride; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoromethanesulfonic acid anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile; 10.1: Sonogashira coupling;
DOI:10.1021/ja066743n

Reference yield:

: 922499-10-3
(2R,3S,4S)-2,3,5-Tris-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-pentan-1-ol

: 922163-77-7
(5R,6R,7R,8S)-8-Azido-6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine

Guidance literature:: Multi-step reaction with 13 steps

1.1: 93 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -60 - 0 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -20 - 20 °C

2.2: tetrahydrofuran / 1 h / -78 - 20 °C

3.1: trifluoroacetic acid / CHCl₃ / 0.42 h / 20 °C

4.1: 0.86 g / 4-N,N-dimethylaminopyridine; pyridine / 0.5 h / 20 °C

5.1: 90 percent / N-iodosuccinimide / acetonitrile / 12 h / 20 °C

6.1: 96 percent / aq. HCl / dioxane / 2 h / 20 °C

7.1: 89 percent / trifluoromethanesulfonic anhydride; pyridine / CH₂Cl₂ / -15 - 50 °C

8.1: sodium methoxide / CH₂Cl₂ / 0.17 h / 20 °C

9.1: 0.822 g / diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 - 20 °C

10.1: 93 percent / EtMgBr / tetrahydrofuran / 0.17 h / 0 °C

11.1: 96 percent / Et₃N; CuI; Pd(PPh₃)4 / dimethylformamide / 16 h / 80 °C

12.1: 76 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

13.1: 92 percent / diphenylphosphoryl azide; DBU / toluene / 4 h / 20 °C

With pyridine; hydrogenchloride; dmap; N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; oxalyl dichloride; diphenylphosphoranyl azide; ethylmagnesium bromide; tetrabutyl ammonium fluoride; sodium methylate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoromethanesulfonic acid anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Swern oxidation / 11.1: Sonogashira coupling;
DOI:10.1021/ja066743n