5-(N-benzyl-N-benzyloxycarbonylamino)-2-bromopent-2(Z)-enoic acid methyl ester

Base Information

• Chemical Name: 5-(N-benzyl-N-benzyloxycarbonylamino)-2-bromopent-2(Z)-enoic acid methyl ester
• CAS No.: 155530-52-2
• Molecular Formula: C₂₁H₂₂BrNO₄
• Molecular Weight: 432.314

Synonyms:5-(N-benzyl-N-benzyloxycarbonylamino)-2-bromopent-2(Z)-enoic acid methyl ester

Chemical Property of 5-(N-benzyl-N-benzyloxycarbonylamino)-2-bromopent-2(Z)-enoic acid methyl ester

Chemical Property:

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Technology Process of 5-(N-benzyl-N-benzyloxycarbonylamino)-2-bromopent-2(Z)-enoic acid methyl ester

There total 3 articles about 5-(N-benzyl-N-benzyloxycarbonylamino)-2-bromopent-2(Z)-enoic acid methyl 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: 93.0%

benzyl benzyl(3-oxopropyl)carbamate (155530-49-7) + methyl 2-bromo-2-(triphenylphosphanylidene)acetate (13504-77-3) → 5-(N-benzyl-N-benzyloxycarbonylamino)-2-bromopent-2(Z)-enoic acid methyl ester (155530-52-2) + 5-(N-benzyl-N-benzyloxycarbonylamino)-2-bromopent-2(E)-enoic acid methyl ester

Guidance literature:

In dichloromethane; at 20 ℃;

DOI:10.1021/ja0202964

Reference yield: 92.0%

benzyl benzyl(3-oxopropyl)carbamate (155530-49-7) + methyl 2-bromo-2-(triphenylphosphanylidene)acetate (13504-77-3) → 5-(N-benzyl-N-benzyloxycarbonylamino)-2-bromopent-2(Z)-enoic acid methyl ester (155530-52-2)

Guidance literature:

In tetrahydrofuran; for 12h; Ambient temperature;

DOI:10.1016/S0040-4039(00)75792-3

Reference yield:

benzyl N-benzyl-N-(3-butenyl)carbamate (123934-05-4) → 5-(N-benzyl-N-benzyloxycarbonylamino)-2-bromopent-2(Z)-enoic acid methyl ester (155530-52-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃; 2.) Zn / 1.) CH₂Cl₂, -78 deg C, 1 h; 2.) AcOH, up to RT

2: 92 percent / tetrahydrofuran / 12 h / Ambient temperature

With ozone; zinc; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)75792-3

upstream raw materials:

benzyl benzyl(3-oxopropyl)carbamate

methyl 2-bromo-2-(triphenylphosphanylidene)acetate

benzyl N-benzyl-N-(3-butenyl)carbamate

Downstream raw materials:

1-ethyl 8-methyl (3aS,7aR,10aS)-5-benzyl-4-oxo-2,3,5,6,7,7a,10,10a-octahydropyrrolo[2.3-i]isoquinoline-1,8(4H)-dicarboxylate

5-(N-benzylamino)-2-vinylpent-2(E)-enoic acid methyl ester

methyl (2R,3aS,7aR,10aS)-5-benzyl-1-(hex-5-enoyl)-4-oxo-2-vinyl-1,2,3,4,5,6,7,7a,10,10a-decahydropyrrolo[2.3-i]isoquinoline-8-carboxylate

methyl (2R,3aS,7aR,10aS)-5-benzyl-2-hydroxymethyl-1-(hex-5-enoyl)-4-oxo1,2,3,4,5,6,7,7a,10,10a-decahydropyrrolo[2.3-i]isoquinoline-8-carboxylate

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