p-nitrobenzyl (1R,5S,6S)-2-[N-[4-(N-p-nitrobenzyloxycarbonylaminomethyl)benzyl]-N-p-nitrobenzyloxycarbonylaminoethylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Base Information

Chemical Name:p-nitrobenzyl (1R,5S,6S)-2-[N-[4-(N-p-nitrobenzyloxycarbonylaminomethyl)benzyl]-N-p-nitrobenzyloxycarbonylaminoethylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate
CAS No.:442681-65-4
Molecular Formula:C₄₃H₄₂N₆O₁₄S
Molecular Weight:898.904
Hs Code.:

p-nitrobenzyl (1R,5S,6S)-2-[N-[4-(N-p-nitrobenzyloxycarbonylaminomethyl)benzyl]-N-p-nitrobenzyloxycarbonylaminoethylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Synonyms:p-nitrobenzyl (1R,5S,6S)-2-[N-[4-(N-p-nitrobenzyloxycarbonylaminomethyl)benzyl]-N-p-nitrobenzyloxycarbonylaminoethylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

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Chemical Property of p-nitrobenzyl (1R,5S,6S)-2-[N-[4-(N-p-nitrobenzyloxycarbonylaminomethyl)benzyl]-N-p-nitrobenzyloxycarbonylaminoethylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

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Technology Process of p-nitrobenzyl (1R,5S,6S)-2-[N-[4-(N-p-nitrobenzyloxycarbonylaminomethyl)benzyl]-N-p-nitrobenzyloxycarbonylaminoethylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

There total 12 articles about p-nitrobenzyl (1R,5S,6S)-2-[N-[4-(N-p-nitrobenzyloxycarbonylaminomethyl)benzyl]-N-p-nitrobenzyloxycarbonylaminoethylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-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:

: 93711-81-0,90776-59-3,189188-38-3
(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

: (2-mercapto-ethyl)-{4-[(4-nitro-benzyloxycarbonylamino)-methyl]-benzyl}-carbamic acid 4-nitro-benzyl ester

: 442681-65-4
p-nitrobenzyl (1R,5S,6S)-2-[N-[4-(N-p-nitrobenzyloxycarbonylaminomethyl)benzyl]-N-p-nitrobenzyloxycarbonylaminoethylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 6 ℃;
DOI:10.1016/S0968-0896(01)00430-8

Reference yield:

: 196880-47-4
4-({[tert-butyl(diphenyl)silyl]oxy}methyl)benzaldehyde

: 442681-65-4
p-nitrobenzyl (1R,5S,6S)-2-[N-[4-(N-p-nitrobenzyloxycarbonylaminomethyl)benzyl]-N-p-nitrobenzyloxycarbonylaminoethylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

1: Na(OAc)3BH; AcOH / tetrahydrofuran / 20 h / 20 °C

2: 2.08 g / aq. NaOH / dioxane; H₂O / pH 8 - 10

3: DMAP / pyridine / 18 h / 20 °C

4: TBAF / tetrahydrofuran / 1 h / 20 °C

5: iPr₂NEt / tetrahydrofuran / 0.5 h / 0 °C

6: NaN₃ / dimethylformamide / 1 h / 20 °C

7: PPh₃; H₂O / tetrahydrofuran / 14 h / 20 °C

8: 990 mg / aq. NaOH / dioxane; H₂O / 0 °C / pH 8.5

9: 73.5 percent / aq. NaOH / methanol / 0.5 h / 20 °C

10: 33.7 percent / PPh₃; DIAD / tetrahydrofuran / 0.5 h / 0 °C

11: aq. NaOH / methanol; tetrahydrofuran / 0.33 h / 0 °C

12: 267 mg / iPr₂NEt / acetonitrile / 6 °C

With dmap; sodium hydroxide; sodium azide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; water; sodium tris(acetoxy)borohydride; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0968-0896(01)00430-8

Reference yield:

: acetic acid 2-[(4-hydroxymethyl-benzyl)-(4-nitro-benzyloxycarbonyl)-amino]-ethyl ester

: 442681-65-4
p-nitrobenzyl (1R,5S,6S)-2-[N-[4-(N-p-nitrobenzyloxycarbonylaminomethyl)benzyl]-N-p-nitrobenzyloxycarbonylaminoethylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: iPr₂NEt / tetrahydrofuran / 0.5 h / 0 °C

2: NaN₃ / dimethylformamide / 1 h / 20 °C

3: PPh₃; H₂O / tetrahydrofuran / 14 h / 20 °C

4: 990 mg / aq. NaOH / dioxane; H₂O / 0 °C / pH 8.5

5: 73.5 percent / aq. NaOH / methanol / 0.5 h / 20 °C

6: 33.7 percent / PPh₃; DIAD / tetrahydrofuran / 0.5 h / 0 °C

7: aq. NaOH / methanol; tetrahydrofuran / 0.33 h / 0 °C

8: 267 mg / iPr₂NEt / acetonitrile / 6 °C

With sodium hydroxide; sodium azide; di-isopropyl azodicarboxylate; water; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0968-0896(01)00430-8