p-nitrobenzyl (5R,6S,8R)-2-<(6,7-dihydro-5H-pyrrolo<1,2-c>imidazol-7-yl)thio>-6-(1-hydroxyethyl)-2-penem-3-carboxylate

Base Information

Chemical Name:p-nitrobenzyl (5R,6S,8R)-2-<(6,7-dihydro-5H-pyrrolo<1,2-c>imidazol-7-yl)thio>-6-(1-hydroxyethyl)-2-penem-3-carboxylate
CAS No.:108308-21-0
Molecular Formula:C₂₁H₂₀N₄O₆S₂
Molecular Weight:488.545
Hs Code.:

Synonyms:p-nitrobenzyl (5R,6S,8R)-2-<(6,7-dihydro-5H-pyrrolo<1,2-c>imidazol-7-yl)thio>-6-(1-hydroxyethyl)-2-penem-3-carboxylate

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Chemical Property of p-nitrobenzyl (5R,6S,8R)-2-<(6,7-dihydro-5H-pyrrolo<1,2-c>imidazol-7-yl)thio>-6-(1-hydroxyethyl)-2-penem-3-carboxylate

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Technology Process of p-nitrobenzyl (5R,6S,8R)-2-<(6,7-dihydro-5H-pyrrolo<1,2-c>imidazol-7-yl)thio>-6-(1-hydroxyethyl)-2-penem-3-carboxylate

There total 6 articles about p-nitrobenzyl (5R,6S,8R)-2-<(6,7-dihydro-5H-pyrrolo<1,2-c>imidazol-7-yl)thio>-6-(1-hydroxyethyl)-2-penem-3-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: 99.0%

: (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

: 6,7-Dihydro-5H-pyrrolo[1,2-c]imidazole-7-thiol; compound with trifluoro-methanesulfonic acid

: 108308-21-0
p-nitrobenzyl (5R,6S,8R)-2-<(6,7-dihydro-5H-pyrrolo<1,2-c>imidazol-7-yl)thio>-6-(1-hydroxyethyl)-2-penem-3-carboxylate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at -40 ℃; for 0.5h;
DOI:10.7164/antibiotics.47.357

Reference yield:

: 111157-51-8
(E)-3-(1H-imidazol-4-yl)-2-propenoic acid ethyl ester

: 108308-21-0
p-nitrobenzyl (5R,6S,8R)-2-<(6,7-dihydro-5H-pyrrolo<1,2-c>imidazol-7-yl)thio>-6-(1-hydroxyethyl)-2-penem-3-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 46 percent / tetramethylguanidine / CHCl₃ / 24 h / Ambient temperature

2: CaCl₂, NaBH₄ / propan-2-ol / 5 h / Ambient temperature

3: CCl₄, Ph₃P / 2.5 h / Heating

4: NaI / acetone / 24 h / Heating

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

6: 99 percent / N,N-diisopropylethylamine / dimethylformamide / 0.5 h / -40 °C

With tetrachloromethane; sodium tetrahydroborate; 1,1,3,3-tetramethylguanidine; methoxybenzene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium iodide; calcium chloride; In chloroform; N,N-dimethyl-formamide; isopropyl alcohol; acetone; trifluoroacetic acid;
DOI:10.7164/antibiotics.47.357

Reference yield:

: 108308-94-7
6,7-Dihydro-7-(p-methoxybenzylthio)-5H-pyrrolo[1,2-c]imidazole

: 108308-21-0
p-nitrobenzyl (5R,6S,8R)-2-<(6,7-dihydro-5H-pyrrolo<1,2-c>imidazol-7-yl)thio>-6-(1-hydroxyethyl)-2-penem-3-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

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

2: 99 percent / N,N-diisopropylethylamine / dimethylformamide / 0.5 h / -40 °C

With methoxybenzene; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; trifluoroacetic acid;
DOI:10.7164/antibiotics.47.357