(S)-N^α-benzyloxycarbonyl-Nⁱⁿ-tert-butyloxycarbonyl-3-(indol-4'-yl)-alanine, methyl ester

Base Information

• Chemical Name: (S)-N^α-benzyloxycarbonyl-Nⁱⁿ-tert-butyloxycarbonyl-3-(indol-4'-yl)-alanine, methyl ester
• CAS No.: 460096-20-2
• Molecular Formula: C₂₅H₂₈N₂O₆
• Molecular Weight: 452.507

Synonyms:(S)-N^α-benzyloxycarbonyl-Nⁱⁿ-tert-butyloxycarbonyl-3-(indol-4'-yl)-alanine, methyl ester

Chemical Property of (S)-N^α-benzyloxycarbonyl-Nⁱⁿ-tert-butyloxycarbonyl-3-(indol-4'-yl)-alanine, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (S)-N^α-benzyloxycarbonyl-Nⁱⁿ-tert-butyloxycarbonyl-3-(indol-4'-yl)-alanine, methyl ester

There total 4 articles about (S)-N^α-benzyloxycarbonyl-Nⁱⁿ-tert-butyloxycarbonyl-3-(indol-4'-yl)-alanine, 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: 100.0%

(Z)-Nα-benzyloxycarbonyl-Nin-tert-butyloxycarbonyl-2,3-dehydro-3-(indol-4'-yl)-alanine, methyl ester (460096-31-5) → (S)-Nα-benzyloxycarbonyl-Nin-tert-butyloxycarbonyl-3-(indol-4'-yl)-alanine, methyl ester (460096-20-2)

Guidance literature:

With hydrogen; In methanol; at 25 ℃; for 72h; under 760.051 Torr;

DOI:10.1021/jo025964i

Reference yield:

4-formyl indole (1074-86-8) → (S)-Nα-benzyloxycarbonyl-Nin-tert-butyloxycarbonyl-3-(indol-4'-yl)-alanine, methyl ester (460096-20-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / KO-t-Bu / 72 h / 0 - 20 °C

2: 83 percent / 1,1,3,3-tetramethylguanidine / tetrahydrofuran / 72 h / -78 - 20 °C

3: 100 percent / [Rh(cis,cis-1,5-cyclooctadiene)(S,S)-MeDuPhos)]⁽¹⁺⁾*TfO^(1-); H₂ / methanol / 72 h / 25 °C / 760.05 Torr

With potassium tert-butylate; hydrogen; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; methanol;

DOI:10.1021/jo025964i

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (S)-Nα-benzyloxycarbonyl-Nin-tert-butyloxycarbonyl-3-(indol-4'-yl)-alanine, methyl ester (460096-20-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / KO-t-Bu / 72 h / 0 - 20 °C

2: 83 percent / 1,1,3,3-tetramethylguanidine / tetrahydrofuran / 72 h / -78 - 20 °C

3: 100 percent / [Rh(cis,cis-1,5-cyclooctadiene)(S,S)-MeDuPhos)]⁽¹⁺⁾*TfO^(1-); H₂ / methanol / 72 h / 25 °C / 760.05 Torr

With potassium tert-butylate; hydrogen; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; methanol;

DOI:10.1021/jo025964i

upstream raw materials:

(Z)-N^α-benzyloxycarbonyl-Nⁱⁿ-tert-butyloxycarbonyl-2,3-dehydro-3-(indol-4'-yl)-alanine, methyl ester

4-formyl indole

di-tert-butyl dicarbonate

tert-butyl 4-formyl-1H-indole-1-carboxylate

Downstream raw materials:

(αS)-α-{[(benzyloxy)carbonyl]amino}-1-[(tert-butoxy)carbonyl]-1H-indole-4-propanoic acid

(αS)-α-{[(benzyloxy)carbonyl]amino}-N,N-dimethyl-1H-indole-4-propanamide

(αS)-α-{[(benzyloxy)carbonyl]amino}-1-[(tert-butoxy)carbonyl]-N,N-dimethyl-1H-indole-4-propanamide

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