D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-, (1S)-4-[[(phenylmethoxy)carbonyl]amino]-1-[[2-(trimethylsilyl)ethoxy]carb onyl]butyl ester

Base Information

Chemical Name:D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-, (1S)-4-[[(phenylmethoxy)carbonyl]amino]-1-[[2-(trimethylsilyl)ethoxy]carb onyl]butyl ester
CAS No.:185448-64-0
Molecular Formula:C₃₅H₄₉N₃O₈Si
Molecular Weight:667.875
Hs Code.:
Mol file:185448-64-0.mol

D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-,
(1S)-4-[[(phenylmethoxy)carbonyl]amino]-1-[[2-(trimethylsilyl)ethoxy]carb
onyl]butyl ester

Synonyms:

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Chemical Property of D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-, (1S)-4-[[(phenylmethoxy)carbonyl]amino]-1-[[2-(trimethylsilyl)ethoxy]carb onyl]butyl ester

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Technology Process of D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-, (1S)-4-[[(phenylmethoxy)carbonyl]amino]-1-[[2-(trimethylsilyl)ethoxy]carb onyl]butyl ester

There total 9 articles about D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-, (1S)-4-[[(phenylmethoxy)carbonyl]amino]-1-[[2-(trimethylsilyl)ethoxy]carb onyl]butyl 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:

: 185448-62-8
(S)-5-Benzyloxycarbonylamino-2-{(R)-2-(tert-butoxycarbonyl-methyl-amino)-3-[1-(tert-butyl-dimethyl-silanyl)-1H-indol-3-yl]-propionyloxy}-pentanoic acid 2-trimethylsilanyl-ethyl ester

: 185448-64-0
(S)-5-Benzyloxycarbonylamino-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-3-(1H-indol-3-yl)-propionyloxy]-pentanoic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; silica gel; In tetrahydrofuran; for 0.333333h;
DOI:10.1021/jo9616062

Reference yield:

: 2916-68-9
2-(Trimethylsilyl)ethanol

: 185448-64-0
(S)-5-Benzyloxycarbonylamino-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-3-(1H-indol-3-yl)-propionyloxy]-pentanoic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 24 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, N,N-dimethyl-4-aminopyridine / pyridine / 50 h / 0 - 20 °C

2: 80 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, N,N-dimethyl-4-aminopyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

3: Bu₄NF/SiO₂ / tetrahydrofuran / 0.33 h

With dmap; tetrabutyl ammonium fluoride; silica gel; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1021/jo9616062

Reference yield:

: 70-26-8,25104-12-5,410523-47-6
L-ornithine

: 185448-64-0
(S)-5-Benzyloxycarbonylamino-2-[(R)-2-(tert-butoxycarbonyl-methyl-amino)-3-(1H-indol-3-yl)-propionyloxy]-pentanoic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaNO₂, conc. H₂SO₄, 2.) 2 N NaOH / 1.) water, room temp., 46 h, 2.) water, room temp., 4 h

2: 24 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, N,N-dimethyl-4-aminopyridine / pyridine / 50 h / 0 - 20 °C

3: 80 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride, N,N-dimethyl-4-aminopyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

4: Bu₄NF/SiO₂ / tetrahydrofuran / 0.33 h

With dmap; sodium hydroxide; sulfuric acid; tetrabutyl ammonium fluoride; silica gel; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium nitrite; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1021/jo9616062