(E)-3-Methanesulfonyloxy-2-{(1R,5R)-1-methoxy-3-[(4-nitro-benzyloxycarbonyl)-phenyl-methyl]-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl}-but-2-enoic acid 4-nitro-benzyl ester

Base Information

Chemical Name:(E)-3-Methanesulfonyloxy-2-{(1R,5R)-1-methoxy-3-[(4-nitro-benzyloxycarbonyl)-phenyl-methyl]-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl}-but-2-enoic acid 4-nitro-benzyl ester
CAS No.:117509-21-4
Molecular Formula:C₃₂H₂₈N₄O₁₄S
Molecular Weight:724.659
Hs Code.:

(E)-3-Methanesulfonyloxy-2-{(1R,5R)-1-methoxy-3-[(4-nitro-benzyloxycarbonyl)-phenyl-methyl]-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl}-but-2-enoic acid 4-nitro-benzyl ester

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Chemical Property of (E)-3-Methanesulfonyloxy-2-{(1R,5R)-1-methoxy-3-[(4-nitro-benzyloxycarbonyl)-phenyl-methyl]-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl}-but-2-enoic acid 4-nitro-benzyl ester

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Technology Process of (E)-3-Methanesulfonyloxy-2-{(1R,5R)-1-methoxy-3-[(4-nitro-benzyloxycarbonyl)-phenyl-methyl]-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl}-but-2-enoic acid 4-nitro-benzyl ester

There total 9 articles about (E)-3-Methanesulfonyloxy-2-{(1R,5R)-1-methoxy-3-[(4-nitro-benzyloxycarbonyl)-phenyl-methyl]-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl}-but-2-enoic 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:

: 124-63-0
methanesulfonyl chloride

: (E)-3-Hydroxy-2-{(1R,5R)-1-methoxy-3-[(4-nitro-benzyloxycarbonyl)-phenyl-methyl]-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl}-but-2-enoic acid 4-nitro-benzyl ester

: 117509-21-4,117604-10-1
(E)-3-Methanesulfonyloxy-2-{(1R,5R)-1-methoxy-3-[(4-nitro-benzyloxycarbonyl)-phenyl-methyl]-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl}-but-2-enoic acid 4-nitro-benzyl ester

Guidance literature:: With triethylamine; In ethyl acetate; at 0 ℃; for 1.5h; Yield given;
DOI:10.1139/v88-225

Reference yield:

: 64952-48-3
phenylmalonyl chloride mono p-nitrobenzyl ester

: 117509-21-4,117604-10-1
(E)-3-Methanesulfonyloxy-2-{(1R,5R)-1-methoxy-3-[(4-nitro-benzyloxycarbonyl)-phenyl-methyl]-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl}-but-2-enoic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: propylene oxide, pyridine / CH₂Cl₂ / 3 h / -10 °C

2: 85 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / -20 °C

3: toluene / 5 h / Heating

4: ozone / CH₂Cl₂ / 0.25 h / -78 °C

5: triphenylphosphine / ethyl acetate / 30 h / 0 °C

6: triethylamine / ethyl acetate / 1.5 h / 0 °C

With pyridine; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; methyloxirane; In dichloromethane; ethyl acetate; toluene;
DOI:10.1139/v88-225

Reference yield:

: 77835-07-5
phenylmalonic acid mono-p-nitrobenzyl ester

: 117509-21-4,117604-10-1
(E)-3-Methanesulfonyloxy-2-{(1R,5R)-1-methoxy-3-[(4-nitro-benzyloxycarbonyl)-phenyl-methyl]-7-oxo-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl}-but-2-enoic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: oxalyl chloride, N,N-dimethylformamide / CH₂Cl₂ / 2 h / 22 °C

2: propylene oxide, pyridine / CH₂Cl₂ / 3 h / -10 °C

3: 85 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / -20 °C

4: toluene / 5 h / Heating

5: ozone / CH₂Cl₂ / 0.25 h / -78 °C

6: triphenylphosphine / ethyl acetate / 30 h / 0 °C

7: triethylamine / ethyl acetate / 1.5 h / 0 °C

With pyridine; oxalyl dichloride; ozone; triethylamine; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; methyloxirane; In dichloromethane; ethyl acetate; toluene;
DOI:10.1139/v88-225