methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-oxohex-4-enoate

Base Information

• Chemical Name: methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-oxohex-4-enoate
• CAS No.: 314728-05-7
• Molecular Formula: C₁₅H₁₇NO₅
• Molecular Weight: 291.304
• Mol file: 314728-05-7.mol

Synonyms:methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-oxohex-4-enoate

Chemical Property of methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-oxohex-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-oxohex-4-enoate

There total 3 articles about methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-oxohex-4-enoate 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:

(S)-2-benzyloxycarbonylamino-succinic acid 1-methyl ester (4668-42-2) → methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-oxohex-4-enoate (314728-05-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / BH₃ / tetrahydrofuran / 5.5 h / -5 °C

2: 65 percent / NaOCl; TEMPO; NaBr / NaHCO₃ / toluene; H₂O / 3 h / 0 °C

3: toluene / 4.5 h / 100 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; borane; sodium bromide; sodium hydrogencarbonate; In tetrahydrofuran; water; toluene; 1: Reduction / 2: Oxidation / 3: Wittig reaction;

DOI:10.1021/ol0065423

Reference yield:

(S)-2-benzyloxycarbonylamino-4-hydroxybutyric acid methyl ester (314728-04-6) → methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-oxohex-4-enoate (314728-05-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / NaOCl; TEMPO; NaBr / NaHCO₃ / toluene; H₂O / 3 h / 0 °C

2: toluene / 4.5 h / 100 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium bromide; sodium hydrogencarbonate; In water; toluene; 1: Oxidation / 2: Wittig reaction;

DOI:10.1021/ol0065423

Reference yield:

(triphenylphosphoranylidene)acetaldehyde (2136-75-6) + methyl (S)-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoate (60684-59-5) → methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-oxohex-4-enoate (314728-05-7)

Guidance literature:

In toluene; at 100 ℃; for 4.5h;

DOI:10.1021/ol0065423

upstream raw materials:

(triphenylphosphoranylidene)acetaldehyde

methyl (S)-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoate

(S)-2-benzyloxycarbonylamino-succinic acid 1-methyl ester

(S)-2-benzyloxycarbonylamino-4-hydroxybutyric acid methyl ester

Downstream raw materials:

methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-hydroxyhex-4-enoate

methyl (2S,4E)-2-(benzyloxycarbonylamino)-6-bromohex-4-enoate

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

(2S,5R,2'E,5'S)-2-[5'-(benzyloxycarbonylamino)-5'-carbomethoxy-pent-2-ene]-2,5-dihydro-5-isopropyl-3,6-dimethyloxypyrazine