(S)-2-Benzyloxycarbonylamino-3-(tert-butoxycarbonyl-methyl-amino)-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-3-(tert-butoxycarbonyl-methyl-amino)-propionic acid methyl ester
• CAS No.: 138093-74-0
• Molecular Formula: C₁₈H₂₆N₂O₆
• Molecular Weight: 366.414

Synonyms:(S)-2-Benzyloxycarbonylamino-3-(tert-butoxycarbonyl-methyl-amino)-propionic acid methyl ester

Chemical Property of (S)-2-Benzyloxycarbonylamino-3-(tert-butoxycarbonyl-methyl-amino)-propionic acid methyl ester

Chemical Property:

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Technology Process of (S)-2-Benzyloxycarbonylamino-3-(tert-butoxycarbonyl-methyl-amino)-propionic acid methyl ester

There total 5 articles about (S)-2-Benzyloxycarbonylamino-3-(tert-butoxycarbonyl-methyl-amino)-propionic 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:

methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoate (58457-98-0) → (S)-2-Benzyloxycarbonylamino-3-(tert-butoxycarbonyl-methyl-amino)-propionic acid methyl ester (138093-74-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) CF₃COOH / 1.) CH₂Cl₂, RT, 20 min, 2.) H₂O, RT, 1 h

2: 344 mg / CF₃COOH, triethylsilane / CHCl₃ / 14 h / Ambient temperature

3: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

With triethylsilane; triethylamine; trifluoroacetic acid; In dichloromethane; chloroform;

DOI:10.1021/ja00029a031

Reference yield:

(S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid (35761-26-3) → (S)-2-Benzyloxycarbonylamino-3-(tert-butoxycarbonyl-methyl-amino)-propionic acid methyl ester (138093-74-0)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / tetrahydrofuran; H₂O / 5 h / Ambient temperature

2: diethyl ether / 0.17 h / Ambient temperature

3: 1.) CF₃COOH / 1.) CH₂Cl₂, RT, 20 min, 2.) H₂O, RT, 1 h

4: 344 mg / CF₃COOH, triethylsilane / CHCl₃ / 14 h / Ambient temperature

5: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

With triethylsilane; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; water;

DOI:10.1021/ja00029a031

Reference yield:

N-[(benzyloxy)carbonyl]-3-[(tert-butoxycarbonyl)amino]-L-alanine (16947-84-5,62234-36-0) → (S)-2-Benzyloxycarbonylamino-3-(tert-butoxycarbonyl-methyl-amino)-propionic acid methyl ester (138093-74-0)

Guidance literature:

Multi-step reaction with 4 steps

1: diethyl ether / 0.17 h / Ambient temperature

2: 1.) CF₃COOH / 1.) CH₂Cl₂, RT, 20 min, 2.) H₂O, RT, 1 h

3: 344 mg / CF₃COOH, triethylsilane / CHCl₃ / 14 h / Ambient temperature

4: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

With triethylsilane; triethylamine; trifluoroacetic acid; In diethyl ether; dichloromethane; chloroform;

DOI:10.1021/ja00029a031

upstream raw materials:

di-tert-butyl dicarbonate

2-benzyloxycarbonylamino-3-methylamino-propionic acid methyl ester

N-[(benzyloxy)carbonyl]-3-[(tert-butoxycarbonyl)amino]-L-alanine

methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoate

Downstream raw materials:

N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-N^β-methyl-L-α,β-diaminopropionic acid

N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-N^β-methyl-L-α,β-diaminopropionylglycyl-N⁵,N⁸-bis(tert-butoxycarbonyl)spermidine

N-(benzyloxycarbonyl)-5,7-isopropylidenegalantinyl-N^β-(tert-butoxycarbonyl)-N^β-methyl-L-α,β-diaminopropionylglycyl-N⁵,N⁸-bis(tert-butoxycarbonyl)spermidine

3-epi-N-(benzyloxycarbonyl)-5,7-isopropylidenegalantinyl-N^β-(tert-butoxycarbonyl)-N^β-methyl-L-α,β-diaminopropionylglycyl-N⁵,N⁸-bis(tert-butoxycarbonyl)spermidine

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