tert-butyl 2-azido-3-(2-benzenesulfinyl-1H-indol-3-yl)-3-(tert-butyldimethylsilanyloxy)propionate

Base Information

Chemical Name:tert-butyl 2-azido-3-(2-benzenesulfinyl-1H-indol-3-yl)-3-(tert-butyldimethylsilanyloxy)propionate
CAS No.:863976-64-1
Molecular Formula:C₂₇H₃₆N₄O₄SSi
Molecular Weight:540.759
Hs Code.:

Synonyms:tert-butyl 2-azido-3-(2-benzenesulfinyl-1H-indol-3-yl)-3-(tert-butyldimethylsilanyloxy)propionate

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Chemical Property of tert-butyl 2-azido-3-(2-benzenesulfinyl-1H-indol-3-yl)-3-(tert-butyldimethylsilanyloxy)propionate

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Technology Process of tert-butyl 2-azido-3-(2-benzenesulfinyl-1H-indol-3-yl)-3-(tert-butyldimethylsilanyloxy)propionate

There total 10 articles about tert-butyl 2-azido-3-(2-benzenesulfinyl-1H-indol-3-yl)-3-(tert-butyldimethylsilanyloxy)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:

: 5059-30-3
2-chloroindole-3-carboxaldehyde

: 863976-64-1
tert-butyl 2-azido-3-(2-benzenesulfinyl-1H-indol-3-yl)-3-(tert-butyldimethylsilanyloxy)propionate

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium hydride / N,N-dimethyl-acetamide

1.2: 83 percent / N,N-dimethyl-acetamide / 2.5 h / 90 °C

2.1: n-butyl lithium / 1,2-dimethoxy-ethane

2.2: 81 percent / 1,2-dimethoxy-ethane / 40 h / Heating

3.1: sodium hydride / tetrahydrofuran / 15 h

4.1: 6.45 g / potassium ferricyanide; potassium carbonate; K₂OsO₂(OH)4 / (DHQ)2PHAL; mathanesulfonamide / 2-methyl-propan-2-ol; H₂O / 15 h

5.1: triethylamine; 4-nitrobenzenesulfonyl chloride / CH₂Cl₂ / 15 h / 0 °C

5.2: sodium azide / acetone; H₂O / 15 h / 60 °C

6.1: 1.40 g / 2,6-lutidine / CH₂Cl₂ / 15 h

7.1: LiOH*H₂O / tetrahydrofuran; H₂O / 15 h

8.1: 52 percent / toluene / 15 h / 55 °C

9.1: 107 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 0.33 h / 0 °C

With 2,6-dimethylpyridine; lithium hydroxide; n-butyllithium; potassium dioxotetrahydroxoosmate(VI); sodium hydride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 4-Nitrobenzenesulfonyl chloride; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl acetamide; water; toluene; tert-butyl alcohol;
DOI:10.1021/jo050896w

Reference yield:

: 863976-63-0
tert-butyl 2-azido-3-(tert-butyldimethylsilanyloxy)-3-(2-phenylsulfanyl-1H-indol-3-yl)propionate

: 863976-64-1
tert-butyl 2-azido-3-(2-benzenesulfinyl-1H-indol-3-yl)-3-(tert-butyldimethylsilanyloxy)propionate

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 0.333333h;
DOI:10.1021/jo050896w

Reference yield:

: 108-98-5
thiophenol

: 863976-64-1
tert-butyl 2-azido-3-(2-benzenesulfinyl-1H-indol-3-yl)-3-(tert-butyldimethylsilanyloxy)propionate

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium hydride / N,N-dimethyl-acetamide

1.2: 83 percent / N,N-dimethyl-acetamide / 2.5 h / 90 °C

2.1: n-butyl lithium / 1,2-dimethoxy-ethane

2.2: 81 percent / 1,2-dimethoxy-ethane / 40 h / Heating

3.1: sodium hydride / tetrahydrofuran / 15 h

4.1: 6.45 g / potassium ferricyanide; potassium carbonate; K₂OsO₂(OH)4 / (DHQ)2PHAL; mathanesulfonamide / 2-methyl-propan-2-ol; H₂O / 15 h

5.1: triethylamine; 4-nitrobenzenesulfonyl chloride / CH₂Cl₂ / 15 h / 0 °C

5.2: sodium azide / acetone; H₂O / 15 h / 60 °C

6.1: 1.40 g / 2,6-lutidine / CH₂Cl₂ / 15 h

7.1: LiOH*H₂O / tetrahydrofuran; H₂O / 15 h

8.1: 52 percent / toluene / 15 h / 55 °C

9.1: 107 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 0.33 h / 0 °C

With 2,6-dimethylpyridine; lithium hydroxide; n-butyllithium; potassium dioxotetrahydroxoosmate(VI); sodium hydride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 4-Nitrobenzenesulfonyl chloride; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl acetamide; water; toluene; tert-butyl alcohol;
DOI:10.1021/jo050896w