(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

Base Information

Chemical Name:(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
CAS No.:357341-55-0
Molecular Formula:C₄₁H₅₅N₅O₁₂SSi
Molecular Weight:870.066
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 4 articles about (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 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: 72.0%

: 357341-54-9
{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

: 357341-55-0
(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

Guidance literature:: {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; With triethyl phosphite; at 50 ℃; for 4h;

In xylene; at 138 ℃; for 12h;
DOI:10.1081/SCC-100000586

Reference yield:

: 161855-96-5
(S)-[1-[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl-2-methylpropyl]carbamic acid (4-nitrophenyl)methyl ester

: 357341-55-0
(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

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93.3 percent / iPr₂NEt / CH₂Cl₂ / 6 h / 20 °C

2.1: 89 percent / DCC; DMAP / CH₂Cl₂ / 55 h / 20 °C

3.1: 82 percent / Et₃N / tetrahydrofuran / 20 °C

4.1: P(OEt)3 / 4 h / 50 °C

4.2: 72 percent / xylene / 12 h / 138 °C

With dmap; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triethyl phosphite; In tetrahydrofuran; dichloromethane;
DOI:10.1081/SCC-100000586

Reference yield:

: 246519-26-6
2,5-anhydro-1-[[[(4-nitrophenyl)methoxy]carbonyl]-L-valyl]amino-1,4-dideoxy-3-thio-D-threo-pentitol

: 357341-55-0
(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

Guidance literature:: Multi-step reaction with 3 steps

1.1: 89 percent / DCC; DMAP / CH₂Cl₂ / 55 h / 20 °C

2.1: 82 percent / Et₃N / tetrahydrofuran / 20 °C

3.1: P(OEt)3 / 4 h / 50 °C

3.2: 72 percent / xylene / 12 h / 138 °C

With dmap; triethylamine; dicyclohexyl-carbodiimide; triethyl phosphite; In tetrahydrofuran; dichloromethane;
DOI:10.1081/SCC-100000586