(pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>penicillanate

Base Information

Chemical Name:(pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>penicillanate
CAS No.:124093-83-0
Molecular Formula:C₂₄H₃₀N₂O₁₀S
Molecular Weight:538.576
Hs Code.:

Synonyms:(pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>penicillanate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>penicillanate

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Technology Process of (pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>penicillanate

There total 4 articles about (pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>penicillanate 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: 97.0%

: 85760-58-3
(pivaloyloxy)methyl 6α-<1(R)-hydroxyethyl>penicillanate

: 4457-32-3
4-nitrobenzyl chloroformate

: 124093-83-0
(pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>penicillanate

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 16h; Ambient temperature;
DOI:10.1021/jm00163a048

Reference yield:

: 18997-19-8
Chloromethyl pivalate

: 124093-83-0
(pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>penicillanate

Guidance literature:: Multi-step reaction with 4 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

With dmap; tert-butylmagnesium chloride; hydrogen; potassium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00163a048

Reference yield:

: 124093-82-9
(pivaloyloxy)methyl 6α-bromo-6β-<1(R)-hydroxyethyl>penicillanate

: 124093-83-0
(pivaloyloxy)methyl 6α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>penicillanate

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / H₂ / 10percent Pd/C / H₂O; tetrahydrofuran / 1.5 h

2: 97 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / Ambient temperature

With dmap; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jm00163a048