(5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-hydroxy-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

Base Information

Chemical Name:(5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-hydroxy-N-phenylimidazo[1,2-a]pyridine-2-carboxamide
CAS No.:917109-71-8
Molecular Formula:C₃₆H₃₅N₃O₅
Molecular Weight:589.691
Hs Code.:

Synonyms:(5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-hydroxy-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

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Chemical Property of (5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-hydroxy-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

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Technology Process of (5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-hydroxy-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

There total 4 articles about (5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-hydroxy-N-phenylimidazo[1,2-a]pyridine-2-carboxamide 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: 93.0%

: 917109-70-7
(5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-N-phenyl-8-[(triisopropylsilyl)oxy]imidazo[1,2-a]pyridine-2-carboxamide

: 917109-71-8
(5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-hydroxy-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 3h;
DOI:10.1039/b612154c

Reference yield:

: 848782-17-2
(5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-(triisopropylsilyl)imidazo[1,2-a]pyridine

: 917109-71-8
(5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-hydroxy-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / N-iodosuccinimide / dimethylformamide / 6 h / 80 °C

2.1: 88 percent / EtMgBr / tetrahydrofuran / 0.17 h / 0 °C

3.1: EtMgBr / tetrahydrofuran / 0.17 h / 0 °C

3.2: 81 percent / tetrahydrofuran / 2.5 h / 0 - 23 °C

4.1: 93 percent / Bu₄NF / tetrahydrofuran / 3 h / 0 °C

With N-iodo-succinimide; ethylmagnesium bromide; tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1039/b612154c

Reference yield:

: 917109-69-4
(5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-iodo-5,6,7,8-tetrahydro-8-[(triisopropylsilyl)oxy]-imidazo[1,2-a]pyridine

: 917109-71-8
(5R,6R,7S,8S)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-8-hydroxy-N-phenylimidazo[1,2-a]pyridine-2-carboxamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: EtMgBr / tetrahydrofuran / 0.17 h / 0 °C

1.2: 81 percent / tetrahydrofuran / 2.5 h / 0 - 23 °C

2.1: 93 percent / Bu₄NF / tetrahydrofuran / 3 h / 0 °C

With ethylmagnesium bromide; tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1039/b612154c