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

Base Information

Chemical Name:methyl 2-azido-3-(tert-butyldimethylsilanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionate
CAS No.:760968-14-7
Molecular Formula:C₂₅H₃₂N₄O₅SSi
Molecular Weight:528.704
Hs Code.:

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

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Chemical Property of methyl 2-azido-3-(tert-butyldimethylsilanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionate

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Technology Process of methyl 2-azido-3-(tert-butyldimethylsilanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionate

There total 4 articles about methyl 2-azido-3-(tert-butyldimethylsilanyloxy)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionate 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: 68.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 760968-12-5
(2S,3S)-2-Azido-3-hydroxy-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester

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

Guidance literature:: (2S,3S)-2-Azido-3-hydroxy-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionic acid methyl ester; With 2,6-dimethylpyridine; In dichloromethane; for 0.0833333h;

t-butyldimethylsiyl triflate; In dichloromethane; for 15h;
DOI:10.1021/ol048974+

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

: 760968-09-0
methyl 2,3-dihydroxy-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-propionate

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

Guidance literature:: Multi-step reaction with 2 steps

1.1: 4-nitrobenzenesulfonyl chloride; Et₃N / CH₂Cl₂ / 15 h / 0 °C

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

2.1: 1.65 g / 2,6-lutidine / CH₂Cl₂ / 15 h

With 2,6-dimethylpyridine; triethylamine; 4-Nitrobenzenesulfonyl chloride; In dichloromethane;
DOI:10.1021/jo050896w