ethyl (5R,6R,7S,8R)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carbonitrile

Base Information

Chemical Name:ethyl (5R,6R,7S,8R)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carbonitrile
CAS No.:644965-52-6
Molecular Formula:C₃₇H₃₅N₃O₄
Molecular Weight:585.703
Hs Code.:

Synonyms:ethyl (5R,6R,7S,8R)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carbonitrile

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Chemical Property of ethyl (5R,6R,7S,8R)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carbonitrile

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Technology Process of ethyl (5R,6R,7S,8R)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carbonitrile

There total 4 articles about ethyl (5R,6R,7S,8R)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carbonitrile 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: 73.0%

: 19158-51-1
P-toluenesulfonyl cyanide

: 644965-24-2
(5R,6R,7S,8R)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-iodoimidazo[1,2-a]pyridine

: 644965-52-6
ethyl (5R,6R,7S,8R)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carbonitrile

Guidance literature:: (5R,6R,7S,8R)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-iodoimidazo[1,2-a]pyridine; With ethylmagnesium bromide; In tetrahydrofuran; at 0 ℃; for 0.25h;

P-toluenesulfonyl cyanide; In tetrahydrofuran; at 0 - 23 ℃; for 4h;
DOI:10.1002/hlca.200390293

Reference yield: 40.0%

: 557-21-1
dicyanozinc

: 644965-24-2
(5R,6R,7S,8R)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydro-2-iodoimidazo[1,2-a]pyridine

: 191863-34-0
(5R,6R,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine

: 644965-52-6
ethyl (5R,6R,7S,8R)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carbonitrile

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 150 ℃; for 1h;
DOI:10.1002/hlca.200390293

Reference yield:

: 191863-34-0
(5R,6R,7S,8R)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine

: 644965-52-6
ethyl (5R,6R,7S,8R)-6,7,8-tris(benzyloxy)-5-[(benzyloxy)methyl]-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-2-carbonitrile

Guidance literature:: Multi-step reaction with 3 steps

1.1: 23 percent / N-iodosuccinimide / dimethylformamide / 8 h / 50 °C

2.1: 88 percent / EtMgBr / trifluoroacetic acid / 0.42 h / 23 °C

3.1: EtMgBr / tetrahydrofuran / 0.25 h / 0 °C

3.2: 73 percent / tetrahydrofuran / 4 h / 0 - 23 °C

With N-iodo-succinimide; ethylmagnesium bromide; In tetrahydrofuran; N,N-dimethyl-formamide; trifluoroacetic acid;
DOI:10.1002/hlca.200390293