N-benzyloxycarbonyl-N'-(tert-butyloxycarbonyl)-Z-α,β-didehydrotryptophan

Base Information

• Chemical Name: N-benzyloxycarbonyl-N'-(tert-butyloxycarbonyl)-Z-α,β-didehydrotryptophan
• CAS No.: 130680-70-5
• Molecular Formula: C₂₅H₂₆N₂O₆
• Molecular Weight: 450.491
• Mol file: 130680-70-5.mol

Synonyms:N-benzyloxycarbonyl-N'-(tert-butyloxycarbonyl)-Z-α,β-didehydrotryptophan

Chemical Property of N-benzyloxycarbonyl-N'-(tert-butyloxycarbonyl)-Z-α,β-didehydrotryptophan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyloxycarbonyl-N'-(tert-butyloxycarbonyl)-Z-α,β-didehydrotryptophan

There total 9 articles about N-benzyloxycarbonyl-N'-(tert-butyloxycarbonyl)-Z-α,β-didehydrotryptophan 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: 49.0%

1-tert-butoxycarbonyl-3-formylindole (57476-50-3) + N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) → N-benzyloxycarbonyl-N'-(tert-butyloxycarbonyl)-Z-α,β-didehydrotryptophan (130680-70-5) + methyl (E)-3-(1-tert-butoxycarbonylindol-3-yl)-2-(carbobenzoxyamino)acrylate (130680-70-5)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; for 2.5h; Ambient temperature;

DOI:10.1007/BF00696717

Reference yield: 49.0%

1-tert-butoxycarbonyl-3-formylindole (57476-50-3) + N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester (100945-15-1,88568-95-0) → N-benzyloxycarbonyl-N'-(tert-butyloxycarbonyl)-Z-α,β-didehydrotryptophan (130680-70-5) + methyl (E)-3-(1-tert-butoxycarbonylindol-3-yl)-2-(carbobenzoxyamino)acrylate (130680-70-5)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; for 2.5h; Ambient temperature;

DOI:10.1007/BF00696717

Reference yield:

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) → N-benzyloxycarbonyl-N'-(tert-butyloxycarbonyl)-Z-α,β-didehydrotryptophan (130680-70-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / K₂CO₃ / acetonitrile / 6 h / Ambient temperature

2: 49 percent / t-BuOK / tetrahydrofuran / 2.5 h / Ambient temperature

With potassium tert-butylate; potassium carbonate; In tetrahydrofuran; acetonitrile;

DOI:10.1007/BF00696717

upstream raw materials:

1-tert-butoxycarbonyl-3-formylindole

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

methyl 2-(benzyloxycarbonylamino)-2-(diethyloxyphosphoryl)acetate

Indole-3-carboxaldehyde

Downstream raw materials:

Cbz-ΔTrp-OMe