(E)-(2S,7S)-2-Amino-7-benzyloxycarbonylamino-oct-4-enedioic acid dimethyl ester

Base Information

Chemical Name:(E)-(2S,7S)-2-Amino-7-benzyloxycarbonylamino-oct-4-enedioic acid dimethyl ester
CAS No.:314728-11-5
Molecular Formula:C₁₈H₂₄N₂O₆
Molecular Weight:364.398
Hs Code.:

Synonyms:(E)-(2S,7S)-2-Amino-7-benzyloxycarbonylamino-oct-4-enedioic acid dimethyl ester

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Chemical Property of (E)-(2S,7S)-2-Amino-7-benzyloxycarbonylamino-oct-4-enedioic acid dimethyl ester

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Technology Process of (E)-(2S,7S)-2-Amino-7-benzyloxycarbonylamino-oct-4-enedioic acid dimethyl ester

There total 7 articles about (E)-(2S,7S)-2-Amino-7-benzyloxycarbonylamino-oct-4-enedioic acid dimethyl 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:

: 4668-42-2
(S)-2-benzyloxycarbonylamino-succinic acid 1-methyl ester

: 314728-11-5
(E)-(2S,7S)-2-Amino-7-benzyloxycarbonylamino-oct-4-enedioic acid dimethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 75 percent / BH₃ / tetrahydrofuran / 5.5 h / -5 °C

2.1: 65 percent / NaOCl; TEMPO; NaBr / NaHCO₃ / toluene; H₂O / 3 h / 0 °C

3.1: toluene / 4.5 h / 100 °C

4.1: 87 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C

5.1: 72 percent / CBr₄; PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

6.2: 89 percent / tetrahydrofuran; hexane / 8 h / -78 °C

7.1: aq. HCl / tetrahydrofuran / 12.5 h

With hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; carbon tetrabromide; borane; triphenylphosphine; sodium bromide; sodium hydrogencarbonate; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 1.1: Reduction / 2.1: Oxidation / 3.1: Wittig reaction / 4.1: Reduction / 5.1: Substitution / 6.1: Metallation / 6.2: Substitution / 7.1: Hydrolysis;
DOI:10.1021/ol0065423

Reference yield:

: 314728-04-6
(S)-2-benzyloxycarbonylamino-4-hydroxybutyric acid methyl ester

: 314728-11-5
(E)-(2S,7S)-2-Amino-7-benzyloxycarbonylamino-oct-4-enedioic acid dimethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 65 percent / NaOCl; TEMPO; NaBr / NaHCO₃ / toluene; H₂O / 3 h / 0 °C

2.1: toluene / 4.5 h / 100 °C

3.1: 87 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C

4.1: 72 percent / CBr₄; PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

5.2: 89 percent / tetrahydrofuran; hexane / 8 h / -78 °C

6.1: aq. HCl / tetrahydrofuran / 12.5 h

With hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; carbon tetrabromide; triphenylphosphine; sodium bromide; sodium hydrogencarbonate; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 1.1: Oxidation / 2.1: Wittig reaction / 3.1: Reduction / 4.1: Substitution / 5.1: Metallation / 5.2: Substitution / 6.1: Hydrolysis;
DOI:10.1021/ol0065423