N-(6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-yl)-isobutyramide

Base Information

Chemical Name:N-(6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-yl)-isobutyramide
CAS No.:922163-78-8
Molecular Formula:C₄₁H₄₁N₃O₄
Molecular Weight:639.794
Hs Code.:

<i>N</i>-(6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-<i>a</i>]pyridin-8-yl)-isobutyramide

Synonyms:N-(6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-yl)-isobutyramide

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Chemical Property of N-(6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-yl)-isobutyramide

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Technology Process of N-(6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-yl)-isobutyramide

There total 17 articles about N-(6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-yl)-isobutyramide 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: 95.0%

: 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

: 97-72-3
2-Methylpropionic anhydride

: 922163-78-8
N-(6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-yl)-isobutyramide

Guidance literature:: (5R,6R,7R,8S)-8-Azido-6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine; With water; triphenylphosphine; In tetrahydrofuran; at 60 ℃; for 3h;

2-Methylpropionic anhydride; With triethylamine; In tetrahydrofuran; water; at 20 ℃; for 1.5h;
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

: 922163-78-8
N-(6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-yl)-isobutyramide

Guidance literature:: Multi-step reaction with 14 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

14.1: PPh₃; H₂O / tetrahydrofuran / 3 h / 60 °C

14.2: 95 percent / Et₃N / tetrahydrofuran; H₂O / 1.5 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; water; sodium methylate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoromethanesulfonic acid anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 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

Reference yield:

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

: 922163-78-8
N-(6,7-bis-benzyloxy-5-benzyloxymethyl-2-phenylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-8-yl)-isobutyramide

Guidance literature:: Multi-step reaction with 13 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

13.1: PPh₃; H₂O / tetrahydrofuran / 3 h / 60 °C

13.2: 95 percent / Et₃N / tetrahydrofuran; H₂O / 1.5 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; water; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoromethanesulfonic acid anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile; 10.1: Sonogashira coupling;
DOI:10.1021/ja066743n