(2S,3R)-2-Benzyloxycarbonylamino-3-[(S)-2-({(S)-1-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-piperidine-2-carbonyl}-amino)-3-phenyl-propionyloxy]-butyric acid methyl ester

Base Information

• Chemical Name: (2S,3R)-2-Benzyloxycarbonylamino-3-[(S)-2-({(S)-1-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-piperidine-2-carbonyl}-amino)-3-phenyl-propionyloxy]-butyric acid methyl ester
• CAS No.: 681254-32-0
• Molecular Formula: C₄₄H₅₃N₅O₁₀
• Molecular Weight: 811.932

Synonyms:

Chemical Property of (2S,3R)-2-Benzyloxycarbonylamino-3-[(S)-2-({(S)-1-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-piperidine-2-carbonyl}-amino)-3-phenyl-propionyloxy]-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-Benzyloxycarbonylamino-3-[(S)-2-({(S)-1-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-piperidine-2-carbonyl}-amino)-3-phenyl-propionyloxy]-butyric acid methyl ester

There total 7 articles about (2S,3R)-2-Benzyloxycarbonylamino-3-[(S)-2-({(S)-1-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-piperidine-2-carbonyl}-amino)-3-phenyl-propionyloxy]-butyric 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-amino-3-phenylpropanoate (2577-90-4) → (2S,3R)-2-Benzyloxycarbonylamino-3-[(S)-2-({(S)-1-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-piperidine-2-carbonyl}-amino)-3-phenyl-propionyloxy]-butyric acid methyl ester (681254-32-0)

Guidance literature:

Multi-step reaction with 5 steps

1: HATU; Hunig's base / acetonitrile

2: 100 percent / TFA; anisole / CH₂Cl₂

3: HATU; Hunig's base / CH₂Cl₂

4: 100 percent / Ba(OH)2 / methanol

5: HATU; TBTU; PyBop / DEPBT; Hunig's base / acetonitrile

With barium dihydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; methoxybenzene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/j.tetlet.2004.01.048

Reference yield:

Boc-Trp-OH (13139-14-5) → (2S,3R)-2-Benzyloxycarbonylamino-3-[(S)-2-({(S)-1-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-piperidine-2-carbonyl}-amino)-3-phenyl-propionyloxy]-butyric acid methyl ester (681254-32-0)

Guidance literature:

Multi-step reaction with 3 steps

1: HATU; Hunig's base / CH₂Cl₂

2: 100 percent / Ba(OH)2 / methanol

3: HATU; TBTU; PyBop / DEPBT; Hunig's base / acetonitrile

With barium dihydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/j.tetlet.2004.01.048

Reference yield:

(S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid (26250-84-0) → (2S,3R)-2-Benzyloxycarbonylamino-3-[(S)-2-({(S)-1-[(S)-2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-piperidine-2-carbonyl}-amino)-3-phenyl-propionyloxy]-butyric acid methyl ester (681254-32-0)

Guidance literature:

Multi-step reaction with 5 steps

1: HATU; Hunig's base / acetonitrile

2: 100 percent / TFA; anisole / CH₂Cl₂

3: HATU; Hunig's base / CH₂Cl₂

4: 100 percent / Ba(OH)2 / methanol

5: HATU; TBTU; PyBop / DEPBT; Hunig's base / acetonitrile

With barium dihydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; methoxybenzene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/j.tetlet.2004.01.048

upstream raw materials:

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate

2-({1-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionyl]-piperidine-2-carbonyl}-amino)-3-phenyl-propionic acid

methyl (2S)-2-amino-3-phenylpropanoate

Boc-Trp-OH

Downstream raw materials:

2-benzyloxycarbonylamino-3-[2-({1-[2-{[1-(2-tert-butoxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-amino}-3-(1H-indol-3-yl)-propionyl]-piperidine-2-carbonyl}-amino)-3-phenyl-propionyloxy]-butyric acid methyl ester

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