{3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[1-(2-{[3-methyl-2-(4-nitro-benzyloxycarbonylamino)-butyrylamino]-methyl}-tetrahydro-furan-3-ylsulfanylcarbonyl)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: {3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[1-(2-{[3-methyl-2-(4-nitro-benzyloxycarbonylamino)-butyrylamino]-methyl}-tetrahydro-furan-3-ylsulfanylcarbonyl)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester
• CAS No.: 357341-54-9
• Molecular Formula: C₄₁H₅₅N₅O₁₄SSi
• Molecular Weight: 902.064

Synonyms:{3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[1-(2-{[3-methyl-2-(4-nitro-benzyloxycarbonylamino)-butyrylamino]-methyl}-tetrahydro-furan-3-ylsulfanylcarbonyl)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester

Chemical Property of {3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[1-(2-{[3-methyl-2-(4-nitro-benzyloxycarbonylamino)-butyrylamino]-methyl}-tetrahydro-furan-3-ylsulfanylcarbonyl)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

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Technology Process of {3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[1-(2-{[3-methyl-2-(4-nitro-benzyloxycarbonylamino)-butyrylamino]-methyl}-tetrahydro-furan-3-ylsulfanylcarbonyl)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester

There total 3 articles about {3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[1-(2-{[3-methyl-2-(4-nitro-benzyloxycarbonylamino)-butyrylamino]-methyl}-tetrahydro-furan-3-ylsulfanylcarbonyl)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic 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: 82.0%

chloroxoacetic acid (4-nitrophenyl)methyl ester (81779-73-9) + S-[(2R,3R)-tetrahydro-2-[[[(S)-3-methyl-2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]-1-oxobutyl]amino]methyl]-3-furanyl](α,2S,3S)-3-[(R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-α-methyl-4-oxo-2-azetidinemethanethiolate (357341-53-8) → {3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[1-(2-{[3-methyl-2-(4-nitro-benzyloxycarbonylamino)-butyrylamino]-methyl}-tetrahydro-furan-3-ylsulfanylcarbonyl)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester (357341-54-9)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃;

DOI:10.1081/SCC-100000586

Reference yield:

(S)-[1-[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl-2-methylpropyl]carbamic acid (4-nitrophenyl)methyl ester (161855-96-5) → {3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[1-(2-{[3-methyl-2-(4-nitro-benzyloxycarbonylamino)-butyrylamino]-methyl}-tetrahydro-furan-3-ylsulfanylcarbonyl)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester (357341-54-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 93.3 percent / iPr₂NEt / CH₂Cl₂ / 6 h / 20 °C

2: 89 percent / DCC; DMAP / CH₂Cl₂ / 55 h / 20 °C

3: 82 percent / Et₃N / tetrahydrofuran / 20 °C

With dmap; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1081/SCC-100000586

Reference yield:

2,5-anhydro-1-[[[(4-nitrophenyl)methoxy]carbonyl]-L-valyl]amino-1,4-dideoxy-3-thio-D-threo-pentitol (246519-26-6) → {3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[1-(2-{[3-methyl-2-(4-nitro-benzyloxycarbonylamino)-butyrylamino]-methyl}-tetrahydro-furan-3-ylsulfanylcarbonyl)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester (357341-54-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / DCC; DMAP / CH₂Cl₂ / 55 h / 20 °C

2: 82 percent / Et₃N / tetrahydrofuran / 20 °C

With dmap; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1081/SCC-100000586

upstream raw materials:

chloroxoacetic acid (4-nitrophenyl)methyl ester

S-[(2R,3R)-tetrahydro-2-[[[(S)-3-methyl-2-[[[(4-nitrophenyl)methoxy]carbonyl]amino]-1-oxobutyl]amino]methyl]-3-furanyl](α,2S,3S)-3-[(R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-α-methyl-4-oxo-2-azetidinemethanethiolate

(S)-[1-[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl-2-methylpropyl]carbamic acid (4-nitrophenyl)methyl ester

2,5-anhydro-1-[[[(4-nitrophenyl)methoxy]carbonyl]-L-valyl]amino-1,4-dideoxy-3-thio-D-threo-pentitol

Downstream raw materials:

(1R,5S,6S)-6-[(R)-1-(tert-butyldimethylsilanyloxyl)ethyl]-2-[[(2R,3R)-2-[[[(S)-2-(4-nitrobenzyloxycarbonyl)amino-3-methyl-1-oxobutyl]amino]methyl]tetrahydro-3-furanyl]thio]-1-methylcarbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester

OCA 983

[1(S),3[4R,5S,6S(R)]]-1-[[[[2-(4-nitrophenyl)methoxy]carbonyl]amino-3-methyl-1-oxobutyl]amino]-2,5-anhydro-3-S-[6-(1-hydroxyethyl)-4-methyl-2-[[(4-nitrophenyl)methoxy]carbonyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]-1,4-dideoxy-3-thio-D-threo-pentitol

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