N_in-L-benzyloxycarbonylalanyl-N_a-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester

Base Information

• Chemical Name: N_in-L-benzyloxycarbonylalanyl-N_a-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester
• CAS No.: 316828-35-0
• Molecular Formula: C₂₆H₂₅Cl₃IN₃O₇
• Molecular Weight: 724.764

Synonyms:N_in-L-benzyloxycarbonylalanyl-N_a-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester

Chemical Property of N_in-L-benzyloxycarbonylalanyl-N_a-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

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Technology Process of N_in-L-benzyloxycarbonylalanyl-N_a-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester

There total 6 articles about N_in-L-benzyloxycarbonylalanyl-N_a-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan 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: 85.0%

Nin-L-benzyloxycarbonylalanyl-Na-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester (316828-31-6) → Nin-L-benzyloxycarbonylalanyl-Na-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester (316828-35-0)

Guidance literature:

N_in-L-benzyloxycarbonylalanyl-N_a-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester; With mercury(II) trifluoroacetate; In dichloromethane; at 20 ℃; for 0.333333h;

With iodine; In dichloromethane; at 20 ℃; for 3h; Further stages.;

DOI:10.1021/ol0067686 DOI:10.1021/jo0264980

Reference yield:

(R)-(+)-tryptophan methyl ester hydrochloride (14907-27-8,5619-09-0,7524-52-9,26988-71-6,41222-70-2,67557-19-1,109492-62-8) → Nin-L-benzyloxycarbonylalanyl-Na-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester (316828-35-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 96 percent / NaHCO₃ / diethyl ether; H₂O / 4 h / 20 °C

2.1: 92 percent / BH₃*THF / tetrahydrofuran; trifluoroacetic acid / 1 h / 0 °C

3.1: DCC / CH₂Cl₂ / 0.33 h / 20 °C

4.1: 3.53 g / DDQ / toluene / 2 h / 110 °C

5.1: Hg(OTFA)2 / CH₂Cl₂ / 0.33 h / 20 °C

5.2: 85 percent / I₂ / CH₂Cl₂ / 3 h / 20 °C

With borane-THF; mercury(II) trifluoroacetate; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; trifluoroacetic acid;

DOI:10.1021/jo0264980

Reference yield:

Nα-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester (316828-30-5) → Nin-L-benzyloxycarbonylalanyl-Na-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester (316828-35-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 92 percent / BH₃*THF / tetrahydrofuran; trifluoroacetic acid / 1 h / 0 °C

2.1: DCC / CH₂Cl₂ / 0.33 h / 20 °C

3.1: 3.53 g / DDQ / toluene / 2 h / 110 °C

4.1: Hg(OTFA)2 / CH₂Cl₂ / 0.33 h / 20 °C

4.2: 85 percent / I₂ / CH₂Cl₂ / 3 h / 20 °C

With borane-THF; mercury(II) trifluoroacetate; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; toluene; trifluoroacetic acid;

DOI:10.1021/jo0264980

upstream raw materials:

N_in-L-benzyloxycarbonylalanyl-N_a-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester

N-Cbz-Ala

(R)-(+)-tryptophan methyl ester hydrochloride

N_α-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester

Downstream raw materials:

N_in-L-benzyloxycarbonylalanyl-N_a-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester

methyl (αR,2S)-2,3-dihydro-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate

C₆₀H₄₉N₅O₉Se

9-(2-{2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionylamino]-benzoylamino}-2-methoxycarbonyl-ethyl)-2-methyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

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