(2S)-2-[N-(tert-butoxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)-O-(4-methylphenylsulfonyl)propan-1-ol

Base Information

Chemical Name:(2S)-2-[N-(tert-butoxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)-O-(4-methylphenylsulfonyl)propan-1-ol
CAS No.:354988-04-8
Molecular Formula:C₂₁H₃₇NO₆SSi
Molecular Weight:459.679
Hs Code.:

Synonyms:(2S)-2-[N-(tert-butoxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)-O-(4-methylphenylsulfonyl)propan-1-ol

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Chemical Property of (2S)-2-[N-(tert-butoxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)-O-(4-methylphenylsulfonyl)propan-1-ol

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Technology Process of (2S)-2-[N-(tert-butoxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)-O-(4-methylphenylsulfonyl)propan-1-ol

There total 1 articles about (2S)-2-[N-(tert-butoxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)-O-(4-methylphenylsulfonyl)propan-1-ol 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: 70.0%

: 98-59-9
p-toluenesulfonyl chloride

: 152491-85-5
(R)-[1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester

: 354988-04-8
(2S)-2-[N-(tert-butoxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)-O-(4-methylphenylsulfonyl)propan-1-ol

Guidance literature:: With dmap; triethylamine; In tetrahydrofuran; at 20 ℃; for 48h;
DOI:10.1021/jo015683v

Reference yield:

: 354988-04-8
(2S)-2-[N-(tert-butoxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)-O-(4-methylphenylsulfonyl)propan-1-ol

: (2S,4R)-4-(tert-butyldimethylsiloxy)-N-(2,4,6-trimethylphenylsulfonyl)-2-(1-phenylvinyl)azetidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 27 percent / NaI / acetone / 24 h / 20 °C

2.1: 1,2-dibromoethane; Zn; TMSCl / dimethylformamide / 0.5 h / 0 °C

2.2: CuCN; LiCl / dimethylformamide; tetrahydrofuran / 0.17 h / -78 °C

2.3: 49 percent / tetrahydrofuran; dimethylformamide / -78 - 0 °C

3.1: CF₃CO₂H / 4 h / 20 °C

4.1: Et₃N / CHCl₃ / 3 h / 20 °C

5.1: 53 percent / K₂CO₃ / Pd(PPh₃)4 / dimethylformamide / 1.5 h / 70 °C

With chloro-trimethyl-silane; potassium carbonate; ethylene dibromide; triethylamine; trifluoroacetic acid; sodium iodide; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In chloroform; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo015683v

Reference yield:

: 354988-04-8
(2S)-2-[N-(tert-butoxycarbonyl)amino]-3-(tert-butyldimethylsiloxy)-O-(4-methylphenylsulfonyl)propan-1-ol

: 354988-11-7
(5R)-6-(tert-butyldimethylsiloxy)-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]hexa-1,2-diene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 27 percent / NaI / acetone / 24 h / 20 °C

2.1: 1,2-dibromoethane; Zn; TMSCl / dimethylformamide / 0.5 h / 0 °C

2.2: CuCN; LiCl / dimethylformamide; tetrahydrofuran / 0.17 h / -78 °C

2.3: 49 percent / tetrahydrofuran; dimethylformamide / -78 - 0 °C

3.1: CF₃CO₂H / 4 h / 20 °C

4.1: Et₃N / CHCl₃ / 3 h / 20 °C

With chloro-trimethyl-silane; ethylene dibromide; triethylamine; trifluoroacetic acid; sodium iodide; zinc; In chloroform; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo015683v