(1S)-2-phenyl-1-{(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl}ethyl naphthalene-2-carboxylate

Base Information

Chemical Name:(1S)-2-phenyl-1-{(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl}ethyl naphthalene-2-carboxylate
CAS No.:263720-40-7
Molecular Formula:C₅₅H₅₀N₂O₆
Molecular Weight:835.012
Hs Code.:

Synonyms:(1S)-2-phenyl-1-{(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl}ethyl naphthalene-2-carboxylate

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Chemical Property of (1S)-2-phenyl-1-{(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl}ethyl naphthalene-2-carboxylate

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Technology Process of (1S)-2-phenyl-1-{(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl}ethyl naphthalene-2-carboxylate

There total 5 articles about (1S)-2-phenyl-1-{(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl}ethyl naphthalene-2-carboxylate 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: 32.0%

: 2-phenyl-1-[(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl]ethanol

: 2243-83-6
2-naphthaloyl chloride

: 263720-40-7
(1S)-2-phenyl-1-{(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl}ethyl naphthalene-2-carboxylate

: 263720-39-4
(1R)-2-phenyl-1-{(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl}ethyl naphthalene-2-carboxylate

Guidance literature:: In pyridine; at 60 ℃; for 6h;
DOI:10.1002/(SICI)1522-2675(20000119)83:1<58::AID-HLCA58>3.0.CO;2-K

Reference yield:

: 191863-33-9
(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)-methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

: 263720-40-7
(1S)-2-phenyl-1-{(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl}ethyl naphthalene-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 24 percent / N-iodosuccinimide / dimethylformamide / 8 h / 60 °C

2.1: 94 percent / EtMgBr / tetrahydrofuran / 0.17 h / 0 °C

3.1: 85 percent / EtMgBr / tetrahydrofuran / 1.5 h / 0 °C

4.1: BuLi; TMEDA / hexane / -78 - 23 °C

4.2: 64 percent / tetrahydrofuran / 1 h / -78 - 23 °C

5.1: 36 percent / pyridine / 6 h / 60 °C

With N-iodo-succinimide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; ethylmagnesium bromide; In tetrahydrofuran; pyridine; hexane; N,N-dimethyl-formamide; 1.1: Iodination / 2.1: Dehalogenation / 3.1: Substitution / 4.1: Metallation / 4.2: Addition / 5.1: Acylation;
DOI:10.1002/(SICI)1522-2675(20000119)83:1<58::AID-HLCA58>3.0.CO;2-K

Reference yield:

: 244138-64-5
(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-2-iodo-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

: 263720-40-7
(1S)-2-phenyl-1-{(5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl}ethyl naphthalene-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 85 percent / EtMgBr / tetrahydrofuran / 1.5 h / 0 °C

2.1: BuLi; TMEDA / hexane / -78 - 23 °C

2.2: 64 percent / tetrahydrofuran / 1 h / -78 - 23 °C

3.1: 36 percent / pyridine / 6 h / 60 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; ethylmagnesium bromide; In tetrahydrofuran; pyridine; hexane; 1.1: Substitution / 2.1: Metallation / 2.2: Addition / 3.1: Acylation;
DOI:10.1002/(SICI)1522-2675(20000119)83:1<58::AID-HLCA58>3.0.CO;2-K