(pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-1-hydroxy-2-methylcarbapen-2-em-3-carboxylate

Base Information

Chemical Name:(pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-1-hydroxy-2-methylcarbapen-2-em-3-carboxylate
CAS No.:80904-03-6
Molecular Formula:C₂₄H₂₈N₂O₁₁
Molecular Weight:520.493
Hs Code.:

Synonyms:(pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-1-hydroxy-2-methylcarbapen-2-em-3-carboxylate

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Chemical Property of (pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-1-hydroxy-2-methylcarbapen-2-em-3-carboxylate

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Technology Process of (pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-1-hydroxy-2-methylcarbapen-2-em-3-carboxylate

There total 12 articles about (pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-1-hydroxy-2-methylcarbapen-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:

: 124093-88-5
(pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-2-methyl-1-oxocarbapen-2-em-3-carboxylate

: 80904-03-6
(pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-1-hydroxy-2-methylcarbapen-2-em-3-carboxylate

Guidance literature:: With tetrabutylammonium borohydride; In dichloromethane; at -78 ℃; for 1h; Yield given;
DOI:10.1021/jm00163a048

Reference yield:

: 18997-19-8
Chloromethyl pivalate

: 80904-03-6
(pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-1-hydroxy-2-methylcarbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1: 12.6 percent / Et₃N, KHCO₃ / dimethylformamide / 21 h / Ambient temperature

2: 1.) tert-BuMgCl, 2.) / 1.) THF, ether, -78 deg C, 1 h, 2.) -78 deg C, 1 h

3: 70 percent / H₂ / 10percent Pd/C / H₂O; tetrahydrofuran / 1.5 h

4: 97 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / Ambient temperature

5: 50 percent / 80percent m-chloroperbenzoic acid / CH₂Cl₂ / 16 h / 0 °C

6: 23 percent / 80percent phosphoric acid, pyridine / dioxane / 20 h / Heating

7: 38 percent / 30percent H₂O₂, formic acid / CH₂Cl₂ / 48 h / Ambient temperature

8: 51 percent / picryl azide, diisopropylethylamine / CH₂Cl₂ / 55.2 h / -10 - 0 °C

9: CH₂Cl₂ / 0.75 h / -55 °C / Irradiation

10: tetrabutylammonium borohydride / CH₂Cl₂ / 1 h / -78 °C

With pyridine; dmap; formic acid; phosphoric acid; 2-azido-1,3,5-trinitro-benzene; tert-butylmagnesium chloride; hydrogen; dihydrogen peroxide; tetrabutylammonium borohydride; potassium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00163a048

Reference yield:

: 69388-93-8
6,6-dibromopenicillanic acid pivaloyloxymethyl ester

: 80904-03-6
(pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-1-hydroxy-2-methylcarbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) tert-BuMgCl, 2.) / 1.) THF, ether, -78 deg C, 1 h, 2.) -78 deg C, 1 h

2: 70 percent / H₂ / 10percent Pd/C / H₂O; tetrahydrofuran / 1.5 h

3: 97 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / Ambient temperature

4: 50 percent / 80percent m-chloroperbenzoic acid / CH₂Cl₂ / 16 h / 0 °C

5: 23 percent / 80percent phosphoric acid, pyridine / dioxane / 20 h / Heating

6: 38 percent / 30percent H₂O₂, formic acid / CH₂Cl₂ / 48 h / Ambient temperature

7: 51 percent / picryl azide, diisopropylethylamine / CH₂Cl₂ / 55.2 h / -10 - 0 °C

8: CH₂Cl₂ / 0.75 h / -55 °C / Irradiation

9: tetrabutylammonium borohydride / CH₂Cl₂ / 1 h / -78 °C

With pyridine; dmap; formic acid; phosphoric acid; 2-azido-1,3,5-trinitro-benzene; tert-butylmagnesium chloride; hydrogen; dihydrogen peroxide; tetrabutylammonium borohydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;
DOI:10.1021/jm00163a048