2-benzyloxycarbonylamino-3-(tert-butyldimethylsilanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid

Base Information

Chemical Name:2-benzyloxycarbonylamino-3-(tert-butyldimethylsilanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid
CAS No.:760967-91-7
Molecular Formula:C₃₂H₃₈N₂O₇SSi
Molecular Weight:622.814
Hs Code.:

Synonyms:2-benzyloxycarbonylamino-3-(tert-butyldimethylsilanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid

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Chemical Property of 2-benzyloxycarbonylamino-3-(tert-butyldimethylsilanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid

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Technology Process of 2-benzyloxycarbonylamino-3-(tert-butyldimethylsilanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid

There total 7 articles about 2-benzyloxycarbonylamino-3-(tert-butyldimethylsilanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid 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: 86.0%

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

: 760967-91-7
2-benzyloxycarbonylamino-3-(tert-butyldimethylsilanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; for 15h;
DOI:10.1021/ol048974+ DOI:10.1021/jo050896w

Reference yield:

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

: 760967-91-7
2-benzyloxycarbonylamino-3-(tert-butyldimethylsilanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid

Guidance literature:: Multi-step reaction with 6 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

6.1: 86 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 15 h

With 2,6-dimethylpyridine; lithium hydroxide; 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

: 760967-91-7
2-benzyloxycarbonylamino-3-(tert-butyldimethylsilanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid

Guidance literature:: Multi-step reaction with 4 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

4: 86 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 15 h

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