(R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanamido)-3-(((triisopropylsilyl)ethynyl)thio)propanoate

Base Information

Chemical Name:(R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanamido)-3-(((triisopropylsilyl)ethynyl)thio)propanoate
CAS No.:1443746-68-6
Molecular Formula:C₃₅H₄₇N₃O₅SSi
Molecular Weight:649.927
Hs Code.:

Synonyms:(R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanamido)-3-(((triisopropylsilyl)ethynyl)thio)propanoate

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Chemical Property of (R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanamido)-3-(((triisopropylsilyl)ethynyl)thio)propanoate

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Technology Process of (R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanamido)-3-(((triisopropylsilyl)ethynyl)thio)propanoate

There total 4 articles about (R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanamido)-3-(((triisopropylsilyl)ethynyl)thio)propanoate 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: 97.0%

: 1443746-72-2
(R)-ethyl 2-((S)-2-((1H-indol-3-yl)methyl)-3-(((benzyloxy)carbonyl)amino)-3-oxopropanamido)-3-mercaptopropanoate

: 181934-30-5
1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one

: 1443746-68-6
(R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanamido)-3-(((triisopropylsilyl)ethynyl)thio)propanoate

Guidance literature:: (R)-ethyl 2-((S)-2-((1H-indol-3-yl)methyl)-3-(((benzyloxy)carbonyl)amino)-3-oxopropanamido)-3-mercaptopropanoate; With L-lysine; L-histidine; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; water; at 20 ℃; for 0.0833333h;

1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one; In tetrahydrofuran; water; at 20 ℃; for 0.00833333h; chemoselective reaction;
DOI:10.1021/ja4044196

Reference yield:

: 7432-21-5
N-carbobenzyloxy-L-tryptophane

: 1443746-68-6
(R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanamido)-3-(((triisopropylsilyl)ethynyl)thio)propanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.17 h / 0 °C

1.2: 17 h / 20 °C

2.1: N,N,N',N'-tetramethylguanidine; L-lysine; L-histidine / tetrahydrofuran; water / 0.08 h / 20 °C

2.2: 0.01 h / 20 °C

With L-lysine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; L-histidine; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ja4044196

Reference yield:

: 107474-02-2
1-(triisopropylsilyl)-2-(trimethylsilyl)acetylene

: 1443746-68-6
(R)-ethyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanamido)-3-(((triisopropylsilyl)ethynyl)thio)propanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0.75 h / 0 °C

1.2: 0.75 h / 0 °C

1.3: 0.25 h

2.1: N,N,N',N'-tetramethylguanidine; L-lysine; L-histidine / tetrahydrofuran; water / 0.08 h / 20 °C

2.2: 0.01 h / 20 °C

With L-lysine; trimethylsilyl trifluoromethanesulfonate; L-histidine; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; water; acetonitrile;
DOI:10.1021/ja4044196