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

Base Information

Chemical Name:2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(2-hydroxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-propionic acid ethyl ester
CAS No.:753487-69-3
Molecular Formula:C₃₁H₄₄N₂O₆Si
Molecular Weight:568.786
Hs Code.:

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

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

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

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

There total 5 articles about 2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(2-hydroxy-1,1-dimethyl-ethyl)-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: 97.0%

: 753488-07-2
3-[1-(2-acetoxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid ethyl ester

: 753487-69-3
2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(2-hydroxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-propionic acid ethyl ester

Guidance literature:: With potassium carbonate; In methanol; at 0 ℃; for 2h;
DOI:10.1021/ol049065n

Reference yield:

: acetic acid 2-indol-1-yl-2-methyl-propyl ester

: 753487-69-3
2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(2-hydroxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: POCl₃ / 0.5 h / 0 °C

1.2: 90 percent / 1.5 h / 20 °C

2.1: NaH / tetrahydrofuran / 1 h / 20 °C

2.2: 90 percent / tetrahydrofuran / 8 h / 20 °C

3.1: NaOH; K₂[OsO₂(OH)4]; t-butyl hypochlorite / propan-1-ol; H₂O / 0.42 h

3.2: (DHQD)2AQH; K₂[OsO₂(OH)4] / propan-1-ol; H₂O / 3 h

4.1: 97 percent / i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C

5.1: 97 percent / K₂CO₃ / methanol / 2 h / 0 °C

With sodium hydroxide; tert-butylhypochlorite; K2; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; trichlorophosphate; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; 2.2: Wittig reaction / 3.2: Sharpless asymmetric aminohydroxylation;
DOI:10.1021/ol049065n

Reference yield:

: 753488-05-0
acetic acid 2-(3-formyl-indol-1-yl)-2-methyl-propyl ester

: 753487-69-3
2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(2-hydroxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: 90 percent / tetrahydrofuran / 8 h / 20 °C

2.1: NaOH; K₂[OsO₂(OH)4]; t-butyl hypochlorite / propan-1-ol; H₂O / 0.42 h

2.2: (DHQD)2AQH; K₂[OsO₂(OH)4] / propan-1-ol; H₂O / 3 h

3.1: 97 percent / i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C

4.1: 97 percent / K₂CO₃ / methanol / 2 h / 0 °C

With sodium hydroxide; tert-butylhypochlorite; K2; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; 1.2: Wittig reaction / 2.2: Sharpless asymmetric aminohydroxylation;
DOI:10.1021/ol049065n