p-nitrobenzyl (5RS,6RS)-2-(2-acetamidoethylthio)-6-<(1-RS)-1-hydroxy-2-(methylsulfonyl)ethyl>-2-carbapenem-3-carboxylate

Base Information

Chemical Name:p-nitrobenzyl (5RS,6RS)-2-(2-acetamidoethylthio)-6-<(1-RS)-1-hydroxy-2-(methylsulfonyl)ethyl>-2-carbapenem-3-carboxylate
CAS No.:98811-29-1
Molecular Formula:C₂₁H₂₅N₃O₉S₂
Molecular Weight:527.576
Hs Code.:

Synonyms:

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Chemical Property of p-nitrobenzyl (5RS,6RS)-2-(2-acetamidoethylthio)-6-<(1-RS)-1-hydroxy-2-(methylsulfonyl)ethyl>-2-carbapenem-3-carboxylate

Chemical Property:

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Useful:

Technology Process of p-nitrobenzyl (5RS,6RS)-2-(2-acetamidoethylthio)-6-<(1-RS)-1-hydroxy-2-(methylsulfonyl)ethyl>-2-carbapenem-3-carboxylate

There total 20 articles about p-nitrobenzyl (5RS,6RS)-2-(2-acetamidoethylthio)-6-<(1-RS)-1-hydroxy-2-(methylsulfonyl)ethyl>-2-carbapenem-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:

: 98810-94-7,109667-64-3,116050-79-4
(3RS,4RS)-3<(1RS)-2-bromo-1-hydroxyethyl>-1-tert-butyldimethylsilyl-4-(2-hydroxyethyl)azetidin-2-one

: 98811-29-1,98856-72-5,98856-74-7,116050-76-1
p-nitrobenzyl (5RS,6RS)-2-(2-acetamidoethylthio)-6-<(1-RS)-1-hydroxy-2-(methylsulfonyl)ethyl>-2-carbapenem-3-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1: 93 percent / potassium fluoride / methanol / 1 h / Ambient temperature

2: 63 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 90 percent / H₂O; dimethylformamide / 1 h / Ambient temperature

4: 73 percent / dimethylaminopyridine / CH₂Cl₂ / 18 h / Ambient temperature

5: 97 percent / 70 percent m-chloroperbenzoic caid / CH₂Cl₂

6: 8 N Jones reagent / acetone

7: 1.) N,N-carbonyldiimidazole / 1.) THF; 2.) THF

8: p-toluenesulfonyl azide, triethylamine / acetonitrile

9: titanium tetrachloride / CH₂Cl₂

10: rhodium(II) diacetate / tetrahydrofuran; benzene

11: 1.) diisopropylethylamine, diphenyl chlorophosphate; 2.) diisopropylethylamine / 1.) acetonitrile; 2.) acetonitirile

With dmap; potassium fluoride; 4-toluenesulfonyl azide; jones reagent; boron trifluoride diethyl etherate; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; chlorophosphoric acid diphenyl ester; 1,1'-carbonyldiimidazole; rhodium(II) acetate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;
DOI:10.1248/cpb.35.996

Reference yield:

: 98810-96-9,109667-65-4,109667-66-5,116050-81-8
(6RS,7RS)-7-<(1RS)-2-bromo-1-hydroxyethyl>-2,2-dimethyl-3-oxa-8-oxo-1-azabicyclo<4.2.0>octane

: 98811-29-1,98856-72-5,98856-74-7,116050-76-1
p-nitrobenzyl (5RS,6RS)-2-(2-acetamidoethylthio)-6-<(1-RS)-1-hydroxy-2-(methylsulfonyl)ethyl>-2-carbapenem-3-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / H₂O; dimethylformamide / 1 h / Ambient temperature

2: 73 percent / dimethylaminopyridine / CH₂Cl₂ / 18 h / Ambient temperature

3: 97 percent / 70 percent m-chloroperbenzoic caid / CH₂Cl₂

4: 8 N Jones reagent / acetone

5: 1.) N,N-carbonyldiimidazole / 1.) THF; 2.) THF

6: p-toluenesulfonyl azide, triethylamine / acetonitrile

7: titanium tetrachloride / CH₂Cl₂

8: rhodium(II) diacetate / tetrahydrofuran; benzene

9: 1.) diisopropylethylamine, diphenyl chlorophosphate; 2.) diisopropylethylamine / 1.) acetonitrile; 2.) acetonitirile

With dmap; 4-toluenesulfonyl azide; jones reagent; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; chlorophosphoric acid diphenyl ester; 1,1'-carbonyldiimidazole; rhodium(II) acetate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;
DOI:10.1248/cpb.35.996

Reference yield:

: 98827-08-8
7-(1-hydroxy-2-methylthioethyl)-2,2-dimethyl-3-oxa-7-phenylthio-1-azabicyclo<4.2.0>octan-8-one

: 98811-29-1,98856-72-5,98856-74-7,116050-76-1
p-nitrobenzyl (5RS,6RS)-2-acetamodoethylthio-6-<1-hydroxy-2-methylsulfonylethyl>-2-carbapenem-3-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 70 percent / azobisisobutyronitrile, triphenyltin hydride / acetone / 19 h / Heating

2: diisopropylethylamine / CH₂Cl₂ / 140 h / Ambient temperature

3: 70 percent m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / 0 °C

4: 82 percent / 8 N Jones reagent / acetone / 7 h / 0 °C

5: 1.) N,N-carbonyldiimidazole / 1.) THF, 6 h, r.t.; 2.) THF, 20 h, r.t.

6: 89 percent / p-toluenesulfonyl azide, triethylamine / acetonitrile / 1 h / Ambient temperature

7: titanium tetrachloride / CH₂Cl₂

8: rhodium(II) diacetate / tetrahydrofuran; benzene

9: 1.) diisopropylethylamine, diphenyl chlorophosphate; 2.) diisopropylethylamine / 1.) acetonitrile; 2.) acetonitirile

With 4-toluenesulfonyl azide; jones reagent; 2,2'-azobis(isobutyronitrile); triphenylstannane; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; chlorophosphoric acid diphenyl ester; 1,1'-carbonyldiimidazole; rhodium(II) acetate; In tetrahydrofuran; dichloromethane; acetone; acetonitrile; benzene;
DOI:10.1248/cpb.35.996