2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

Base Information

Chemical Name:2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester
CAS No.:760968-15-8
Molecular Formula:C₃₃H₄₀N₂O₇SSi
Molecular Weight:636.841
Hs Code.:

2-benzyloxycarbonylamino-3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3-[1-(toluene-4-sulfonyl)-1<i>H</i>-indol-3-yl]-propionic acid methyl ester

Synonyms:2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

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Chemical Property of 2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

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Technology Process of 2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

There total 8 articles about 2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid 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: 35.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 760968-14-7
methyl 2-azido-3-(tert-butyldimethylsilanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionate

: 760968-15-8
2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

Guidance literature:: methyl 2-azido-3-(tert-butyldimethylsilanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionate; With trimethylphosphane; In tetrahydrofuran; for 0.75h;

benzyl chloroformate; In tetrahydrofuran; at -20 - 20 ℃;
DOI:10.1021/ol048974+

Reference yield:

: 464200-92-8
(E)-methyl 3-(1-tosyl-1H-indol-3-yl)acrylate

: 760968-15-8
2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 79 percent / K₂OsO₂(OH)2; potassium ferricyanide; potassium carbonate / (DHQ)2PHAL; methanesulfonamide / 2-methyl-propan-2-ol; H₂O / 15 h

2.1: 4-nitrobenzenesulfonyl chloride; Et₃N / CH₂Cl₂ / 15 h / 0 °C

2.2: sodium azide / dimethylformamide / 15 h / 45 °C

3.1: 1.65 g / 2,6-lutidine / CH₂Cl₂ / 15 h

4.1: trimethylphosphine / tetrahydrofuran / 0.75 h

5.1: 650 mg / tetrahydrofuran / 15 h / 20 °C

With 2,6-dimethylpyridine; K₂OsO₂(OH)2; potassium carbonate; triethylamine; 4-Nitrobenzenesulfonyl chloride; potassium hexacyanoferrate(III); trimethylphosphane; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo050896w

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 760968-15-8
2-benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.65 g / 2,6-lutidine / CH₂Cl₂ / 15 h

2: trimethylphosphine / tetrahydrofuran / 0.75 h

3: 650 mg / tetrahydrofuran / 15 h / 20 °C

With 2,6-dimethylpyridine; trimethylphosphane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo050896w