(5R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-(5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-7-ylsulfanyl)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Base Information

Chemical Name:(5R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-(5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-7-ylsulfanyl)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
CAS No.:108308-80-1
Molecular Formula:C₂₂H₂₂N₄O₆S₂
Molecular Weight:502.572
Hs Code.:

(5R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-(5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-7-ylsulfanyl)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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Chemical Property of (5R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-(5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-7-ylsulfanyl)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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Technology Process of (5R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-(5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-7-ylsulfanyl)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 7 articles about (5R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-(5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-7-ylsulfanyl)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 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:

: (5R,6S)-3-Ethanesulfinyl-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

: 5,6,7,8-Tetrahydro-imidazo[1,2-a]pyridine-7-thiol; compound with trifluoro-methanesulfonic acid

: 108308-80-1
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-(5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-7-ylsulfanyl)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at -40 ℃;
DOI:10.7164/antibiotics.47.357

Reference yield:

: 69619-21-2
5-tert-butoxycarbonylamino-3-oxo-pentanoic acid ethyl ester

: 108308-80-1
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-(5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-7-ylsulfanyl)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 66 percent / NaBH₄ / ethanol / 2 h / 0 - 5 °C

2: N,N'-diethylazodicarboxylate, Ph₃P / tetrahydrofuran / 1.5 h / Ambient temperature

3: 1.) Na/MeOH / 1.) -10 deg C, 1 h, 2.) MeOH, r.t., 1.5 h

4: 1.) CF₃COOH / 1.) anisole, 0-5 deg C, 30 min; 2.) toluene, reflux, 30 min

5: 1.) epichlorohydrin / 2.) CH₂Cl₂, r.t., 1 h

6: 1.) AcOH, 2.) p-CH₃C₆H₄SO₃H*H₂O / 1.) MeOH, reflux, 1 h, 2.) C₆H₆, reflux, 3 h

7: PhOMe / trifluoroacetic acid / 0.5 h / Ambient temperature

8: N,N-diisopropylethylamine / dimethylformamide / -40 °C

With methanol; sodium tetrahydroborate; sodium; toluene-4-sulfonic acid; acetic acid; methoxybenzene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; epichlorohydrin; diethylazodicarboxylate; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; trifluoroacetic acid;
DOI:10.7164/antibiotics.47.357

Reference yield:

: 69619-24-5,182370-56-5
ethyl 5-tert-butoxycarbonylamino-3-hydroxyvalerate

: 108308-80-1
(5R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-(5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-7-ylsulfanyl)-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: N,N'-diethylazodicarboxylate, Ph₃P / tetrahydrofuran / 1.5 h / Ambient temperature

2: 1.) Na/MeOH / 1.) -10 deg C, 1 h, 2.) MeOH, r.t., 1.5 h

3: 1.) CF₃COOH / 1.) anisole, 0-5 deg C, 30 min; 2.) toluene, reflux, 30 min

4: 1.) epichlorohydrin / 2.) CH₂Cl₂, r.t., 1 h

5: 1.) AcOH, 2.) p-CH₃C₆H₄SO₃H*H₂O / 1.) MeOH, reflux, 1 h, 2.) C₆H₆, reflux, 3 h

6: PhOMe / trifluoroacetic acid / 0.5 h / Ambient temperature

7: N,N-diisopropylethylamine / dimethylformamide / -40 °C

With methanol; sodium; toluene-4-sulfonic acid; acetic acid; methoxybenzene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; epichlorohydrin; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide; trifluoroacetic acid;
DOI:10.7164/antibiotics.47.357