2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-propionic acid ethyl ester

Base Information

Chemical Name:2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-propionic acid ethyl ester
CAS No.:753487-71-7
Molecular Formula:C₃₂H₄₄N₂O₅Si
Molecular Weight:564.797
Hs Code.:

2-benzyloxycarbonylamino-3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1<i>H</i>-indol-3-yl]-propionic acid ethyl ester

Synonyms:2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-propionic acid ethyl ester

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Chemical Property of 2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-propionic acid ethyl ester

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Technology Process of 2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-propionic acid ethyl ester

There total 1 articles about 2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-propionic acid ethyl 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: 58.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 753488-09-4
2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-2-oxo-ethyl)-1H-indol-3-yl]-propionic acid ethyl ester

: 753487-71-7
2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-propionic acid ethyl ester

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1h;

2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-2-oxo-ethyl)-1H-indol-3-yl]-propionic acid ethyl ester; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 11h;
DOI:10.1021/ol049065n

Reference yield:

: 753487-71-7
2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-propionic acid ethyl ester

: 855315-83-2
Benzoic acid (2R,4S)-4-((S)-1-allyloxycarbonyl-ethylcarbamoyl)-4-({(2S,3R)-2-amino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-propionyl}-methyl-amino)-2-methyl-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / Et₃SiH; Et₃N / Pd(OAc)2 / CH₂Cl₂ / 20 h / 20 °C

2: LiOH*H₂O / tetrahydrofuran; H₂O / 48 h / 5 °C

3: 210 mg / naHCO₃ / tetrahydrofuran; H₂O / 0 °C

4: 164 mg / i-Pr₂NEt; BOP-Cl / CH₂Cl₂ / 20 °C

5: piperidine / CH₂Cl₂ / 2 h / 20 °C

With piperidine; triethylsilane; lithium hydroxide; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium diacetate; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol049065n

Reference yield:

: 753487-71-7
2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-propionic acid ethyl ester

: 753487-79-5
benzoic acid 4-(1-allyloxycarbonyl-ethylcarbamoyl)-4-{[3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionyl]-methyl-amino}-2-methyl-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / Et₃SiH; Et₃N / Pd(OAc)2 / CH₂Cl₂ / 20 h / 20 °C

2: LiOH*H₂O / tetrahydrofuran; H₂O / 48 h / 5 °C

3: 210 mg / naHCO₃ / tetrahydrofuran; H₂O / 0 °C

4: 164 mg / i-Pr₂NEt; BOP-Cl / CH₂Cl₂ / 20 °C

With triethylsilane; lithium hydroxide; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium diacetate; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol049065n