D-Tryptophan, 2-iodo-1-[N-[(phenylmethoxy)carbonyl]-L-leucyl]-N-[(2,2,2-trichloroethoxy )carbonyl]-, methyl ester

Base Information

Chemical Name:D-Tryptophan, 2-iodo-1-[N-[(phenylmethoxy)carbonyl]-L-leucyl]-N-[(2,2,2-trichloroethoxy )carbonyl]-, methyl ester
CAS No.:316828-36-1
Molecular Formula:C29H31Cl3IN3O7
Molecular Weight:766.845
Hs Code.:
Mol file:316828-36-1.mol

Synonyms:

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Chemical Property of D-Tryptophan, 2-iodo-1-[N-[(phenylmethoxy)carbonyl]-L-leucyl]-N-[(2,2,2-trichloroethoxy )carbonyl]-, methyl ester

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Technology Process of D-Tryptophan, 2-iodo-1-[N-[(phenylmethoxy)carbonyl]-L-leucyl]-N-[(2,2,2-trichloroethoxy )carbonyl]-, methyl ester

There total 6 articles about D-Tryptophan, 2-iodo-1-[N-[(phenylmethoxy)carbonyl]-L-leucyl]-N-[(2,2,2-trichloroethoxy )carbonyl]-, 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%

: 316828-32-7
N_in-L-benzyloxycarbonylleucyl-N_a-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester

: 316828-36-1
N_in-L-benzyloxycarbonylleucyl-N_a-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester

Guidance literature:: N_in-L-benzyloxycarbonylleucyl-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:

: 14907-27-8,5619-09-0,7524-52-9,26988-71-6,41222-70-2,67557-19-1,109492-62-8
(R)-(+)-tryptophan methyl ester hydrochloride

: 316828-36-1
N_in-L-benzyloxycarbonylleucyl-N_a-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester

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: 3.64 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:

: 316828-30-5
N_α-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester

: 316828-36-1
N_in-L-benzyloxycarbonylleucyl-N_a-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester

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: 3.64 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