methyl (2Z,4S)-2-{[(benzyloxy)carbonyl]amino}-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate

Base Information

• Chemical Name: methyl (2Z,4S)-2-{[(benzyloxy)carbonyl]amino}-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate
• CAS No.: 854300-99-5
• Molecular Formula: C₂₅H₃₀N₂O₆
• Molecular Weight: 454.523

Synonyms:methyl (2Z,4S)-2-{[(benzyloxy)carbonyl]amino}-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate

Chemical Property of methyl (2Z,4S)-2-{[(benzyloxy)carbonyl]amino}-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate

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Technology Process of methyl (2Z,4S)-2-{[(benzyloxy)carbonyl]amino}-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate

There total 5 articles about methyl (2Z,4S)-2-{[(benzyloxy)carbonyl]amino}-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-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: 97.0%

Boc-L-phenylalaninal (72155-45-4) + N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) → methyl (2Z,4S)-2-{[(benzyloxy)carbonyl]amino}-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate (854300-99-5)

Guidance literature:

With diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; toluene; at 25 ℃; for 3h;

DOI:10.1016/j.tetlet.2005.03.067

Reference yield: 25.0%

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester (51987-73-6) + N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) → 5-benzyl-3-benzyloxycarbonylamino-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester + methyl (2Z,4S)-2-{[(benzyloxy)carbonyl]amino}-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate (854300-99-5)

Guidance literature:

With n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; toluene; at -78 - 20 ℃; for 5h;

DOI:10.1016/j.tetlet.2005.03.067

Reference yield: 17.0%

Boc-L-phenylalaninal (72155-45-4) + N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) → 5-benzyl-3-benzyloxycarbonylamino-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester + methyl (2Z,4S)-2-{[(benzyloxy)carbonyl]amino}-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate (854300-99-5)

Guidance literature:

With n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; toluene; at -78 - 25 ℃; for 3h;

DOI:10.1016/j.tetlet.2005.03.067

upstream raw materials:

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

Boc-L-phenylalaninal

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

[(1S,3S)-3-(4-Chloro-benzylamino)-4-phenyl-1-(piperidine-1-carbonyl)-butyl]-carbamic acid benzyl ester

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