<(5S)-5-p-nitrobenzyloxycarbonylamino-5-p-nitrobenzyloxycarbonyl>-2-oxapentanoyl-3-bromo-2-methoxy-(2R/S)-alaninyl-(2R)-valine p-nitrobenzyl ester

Base Information

Chemical Name:<(5S)-5-p-nitrobenzyloxycarbonylamino-5-p-nitrobenzyloxycarbonyl>-2-oxapentanoyl-3-bromo-2-methoxy-(2R/S)-alaninyl-(2R)-valine p-nitrobenzyl ester
CAS No.:126167-01-9
Molecular Formula:C₃₆H₃₉BrN₆O₁₆
Molecular Weight:891.64
Hs Code.:

<(5S)-5-p-nitrobenzyloxycarbonylamino-5-p-nitrobenzyloxycarbonyl>-2-oxapentanoyl-3-bromo-2-methoxy-(2R/S)-alaninyl-(2R)-valine p-nitrobenzyl ester

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Chemical Property of <(5S)-5-p-nitrobenzyloxycarbonylamino-5-p-nitrobenzyloxycarbonyl>-2-oxapentanoyl-3-bromo-2-methoxy-(2R/S)-alaninyl-(2R)-valine p-nitrobenzyl ester

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Technology Process of <(5S)-5-p-nitrobenzyloxycarbonylamino-5-p-nitrobenzyloxycarbonyl>-2-oxapentanoyl-3-bromo-2-methoxy-(2R/S)-alaninyl-(2R)-valine p-nitrobenzyl ester

There total 10 articles about <(5S)-5-p-nitrobenzyloxycarbonylamino-5-p-nitrobenzyloxycarbonyl>-2-oxapentanoyl-3-bromo-2-methoxy-(2R/S)-alaninyl-(2R)-valine p-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: 91.0%

: 67-56-1
methanol

: 126167-00-8
<(5S)-5-p-nitrobenzyloxycarbonylamino-5-p-nitrobenzyloxycarbonyl>-2-oxapentanoyl didehydroalaninyl-(2R)-valine p-nitrobenzyl ester

: 126167-01-9,127470-79-5
<(5S)-5-p-nitrobenzyloxycarbonylamino-5-p-nitrobenzyloxycarbonyl>-2-oxapentanoyl-3-bromo-2-methoxy-(2R/S)-alaninyl-(2R)-valine p-nitrobenzyl ester

Guidance literature:: With bromine; In dichloromethane; at -10 ℃; for 0.333333h;
DOI:10.1016/S0040-4020(01)80113-7

Reference yield:

: 95307-20-3
(2R)-valine-p-nitrobenzyl ester

: 126167-01-9,127470-79-5
<(5S)-5-p-nitrobenzyloxycarbonylamino-5-p-nitrobenzyloxycarbonyl>-2-oxapentanoyl-3-bromo-2-methoxy-(2R/S)-alaninyl-(2R)-valine p-nitrobenzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / EEDQ / CH₂Cl₂ / 24 h / Ambient temperature

2: 87 percent / 48percent HBr / acetic acid; CH₂Cl₂ / 1 h / 10 °C

3: 70 percent / dimethylaminopyridine / acetonitrile / 48 h / 40 - 45 °C

4: mCPBA / CH₂Cl₂ / 0.75 h / Ambient temperature

5: xylene / 4 h / 150 °C

6: 91 percent / Br₂ / CH₂Cl₂ / 0.33 h / -10 °C

With dmap; hydrogen bromide; bromine; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetic acid; acetonitrile; xylene;
DOI:10.1016/S0040-4020(01)80113-7

Reference yield:

: 126166-96-9
N-(4-nitrobenzyloxycarbonyl)-L-homoserine lactone

: 126167-01-9,127470-79-5
<(5S)-5-p-nitrobenzyloxycarbonylamino-5-p-nitrobenzyloxycarbonyl>-2-oxapentanoyl-3-bromo-2-methoxy-(2R/S)-alaninyl-(2R)-valine p-nitrobenzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: NaOH / methanol

2: NaI / dimethylformamide / 65 deg C, 10 min, then RT, 1.5 h

3: 63 percent / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 70 percent / dimethylaminopyridine / acetonitrile / 48 h / 40 - 45 °C

5: mCPBA / CH₂Cl₂ / 0.75 h / Ambient temperature

6: xylene / 4 h / 150 °C

7: 91 percent / Br₂ / CH₂Cl₂ / 0.33 h / -10 °C

With dmap; sodium hydroxide; bromine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; xylene;
DOI:10.1016/S0040-4020(01)80113-7