3-[(1S,2S)-2-Azido-1-(tert-butyl-dimethyl-silanyloxy)-2-methoxycarbonyl-ethyl]-2-phenylsulfanyl-indole-1-carboxylic acid benzyl ester

Base Information

Chemical Name:3-[(1S,2S)-2-Azido-1-(tert-butyl-dimethyl-silanyloxy)-2-methoxycarbonyl-ethyl]-2-phenylsulfanyl-indole-1-carboxylic acid benzyl ester
CAS No.:760968-21-6
Molecular Formula:C₃₂H₃₆N₄O₅SSi
Molecular Weight:616.813
Hs Code.:

Synonyms:3-[(1S,2S)-2-Azido-1-(tert-butyl-dimethyl-silanyloxy)-2-methoxycarbonyl-ethyl]-2-phenylsulfanyl-indole-1-carboxylic acid benzyl ester

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Chemical Property of 3-[(1S,2S)-2-Azido-1-(tert-butyl-dimethyl-silanyloxy)-2-methoxycarbonyl-ethyl]-2-phenylsulfanyl-indole-1-carboxylic acid benzyl ester

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Technology Process of 3-[(1S,2S)-2-Azido-1-(tert-butyl-dimethyl-silanyloxy)-2-methoxycarbonyl-ethyl]-2-phenylsulfanyl-indole-1-carboxylic acid benzyl ester

There total 7 articles about 3-[(1S,2S)-2-Azido-1-(tert-butyl-dimethyl-silanyloxy)-2-methoxycarbonyl-ethyl]-2-phenylsulfanyl-indole-1-carboxylic acid benzyl 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:

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

: 760968-21-6
3-[(1S,2S)-2-Azido-1-(tert-butyl-dimethyl-silanyloxy)-2-methoxycarbonyl-ethyl]-2-phenylsulfanyl-indole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

: 108-98-5
thiophenol

: 760968-21-6
3-[(1S,2S)-2-Azido-1-(tert-butyl-dimethyl-silanyloxy)-2-methoxycarbonyl-ethyl]-2-phenylsulfanyl-indole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

: 760968-02-3
2-phenylsulfanyl-1H-indole-3-carbaldehyde

: 760968-21-6
3-[(1S,2S)-2-Azido-1-(tert-butyl-dimethyl-silanyloxy)-2-methoxycarbonyl-ethyl]-2-phenylsulfanyl-indole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

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

1.2: 81 percent / 1,2-dimethoxy-ethane / 40 h / Heating

2.1: sodium hydride / tetrahydrofuran / 15 h

3.1: 6.45 g / potassium ferricyanide; potassium carbonate; K₂OsO₂(OH)4 / (DHQ)2PHAL; mathanesulfonamide / 2-methyl-propan-2-ol; H₂O / 15 h

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

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

5.1: 1.40 g / 2,6-lutidine / CH₂Cl₂ / 15 h

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