(2S,3S,5RS)-2-tert-butoxycarbonylamino-3-tert-butyldiphenylsilyloxy-5-p-tolylsulfonyl-1-triisopropylsilyloxyoctadecan-4-one

Base Information

Chemical Name:(2S,3S,5RS)-2-tert-butoxycarbonylamino-3-tert-butyldiphenylsilyloxy-5-p-tolylsulfonyl-1-triisopropylsilyloxyoctadecan-4-one
CAS No.:244777-36-4
Molecular Formula:C₅₅H₈₉NO₇SSi₂
Molecular Weight:964.551
Hs Code.:

Synonyms:(2S,3S,5RS)-2-tert-butoxycarbonylamino-3-tert-butyldiphenylsilyloxy-5-p-tolylsulfonyl-1-triisopropylsilyloxyoctadecan-4-one

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Chemical Property of (2S,3S,5RS)-2-tert-butoxycarbonylamino-3-tert-butyldiphenylsilyloxy-5-p-tolylsulfonyl-1-triisopropylsilyloxyoctadecan-4-one

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Technology Process of (2S,3S,5RS)-2-tert-butoxycarbonylamino-3-tert-butyldiphenylsilyloxy-5-p-tolylsulfonyl-1-triisopropylsilyloxyoctadecan-4-one

There total 9 articles about (2S,3S,5RS)-2-tert-butoxycarbonylamino-3-tert-butyldiphenylsilyloxy-5-p-tolylsulfonyl-1-triisopropylsilyloxyoctadecan-4-one 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%

: 95049-19-7
4-tolyl tetradecylsulfone

: 244777-35-3
(3S,4S)-N-tert-butoxycarbonyl-3-tert-butyldiphenylsilyloxy-4-(triisopropylsilyloxy)methylazetidin-2-one

: 244777-36-4
(2S,3S,5RS)-2-tert-butoxycarbonylamino-3-tert-butyldiphenylsilyloxy-5-p-tolylsulfonyl-1-triisopropylsilyloxyoctadecan-4-one

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1016/S0040-4039(99)01906-1

Reference yield:

: (2R,3S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-oxo-azetidine-2-carboxylic acid benzyl ester

: 244777-36-4
(2S,3S,5RS)-2-tert-butoxycarbonylamino-3-tert-butyldiphenylsilyloxy-5-p-tolylsulfonyl-1-triisopropylsilyloxyoctadecan-4-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 73 percent / sodium borohydride / ethanol / 1 h / 20 °C

2.1: 95 percent / imidazole / dimethylformamide / 4 h / 20 °C

3.1: 100 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 1 h / 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h

4.2: 86 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; n-butyllithium; triethylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00915-2

Reference yield:

: 13154-24-0
triisopropylsilyl chloride

: 244777-36-4
(2S,3S,5RS)-2-tert-butoxycarbonylamino-3-tert-butyldiphenylsilyloxy-5-p-tolylsulfonyl-1-triisopropylsilyloxyoctadecan-4-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 95 percent / imidazole / dimethylformamide / 4 h / 20 °C

2.1: 100 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 1 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h

3.2: 86 percent / tetrahydrofuran; hexane / 1 h / -78 °C

With 1H-imidazole; dmap; n-butyllithium; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00915-2