(4S)-3-[(2S,4R)-2-azido-5-tert-butyldiphenylsilyloxy-4-methylpentanoyl]-4-phenyloxazolidin-2-one

Base Information

Chemical Name:(4S)-3-[(2S,4R)-2-azido-5-tert-butyldiphenylsilyloxy-4-methylpentanoyl]-4-phenyloxazolidin-2-one
CAS No.:445483-91-0
Molecular Formula:C₃₁H₃₆N₄O₄Si
Molecular Weight:556.737
Hs Code.:

Synonyms:(4S)-3-[(2S,4R)-2-azido-5-tert-butyldiphenylsilyloxy-4-methylpentanoyl]-4-phenyloxazolidin-2-one

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Chemical Property of (4S)-3-[(2S,4R)-2-azido-5-tert-butyldiphenylsilyloxy-4-methylpentanoyl]-4-phenyloxazolidin-2-one

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Technology Process of (4S)-3-[(2S,4R)-2-azido-5-tert-butyldiphenylsilyloxy-4-methylpentanoyl]-4-phenyloxazolidin-2-one

There total 6 articles about (4S)-3-[(2S,4R)-2-azido-5-tert-butyldiphenylsilyloxy-4-methylpentanoyl]-4-phenyloxazolidin-2-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: 82.0%

: 445483-90-9
(4S)-3-[(4R)-5-tert-butyldiphenylsilyloxy-4-methylpentanoyl]-4-phenyloxazolidin-2-one

: 445483-91-0
(4S)-3-[(2S,4R)-2-azido-5-tert-butyldiphenylsilyloxy-4-methylpentanoyl]-4-phenyloxazolidin-2-one

Guidance literature:: (4S)-3-[(4R)-5-tert-butyldiphenylsilyloxy-4-methylpentanoyl]-4-phenyloxazolidin-2-one; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃;

With 2,4,6-Triisopropylbenzenesulfonyl azide; In tetrahydrofuran; at -78 ℃;

With acetic acid; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/S0040-4039(02)00607-X

Reference yield:

: 95514-03-7
(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester

: 445483-91-0
(4S)-3-[(2S,4R)-2-azido-5-tert-butyldiphenylsilyloxy-4-methylpentanoyl]-4-phenyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / DIBAL-H / toluene; diethyl ether / 1.25 h / -80 °C

2.1: 70 percent / (i-Pr)2NEt; LiCl / acetonitrile / 24 h / 20 °C

3.1: 100 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C

4.1: KHMDS / tetrahydrofuran; toluene / 0.67 h / -80 °C

4.2: trisyl azide / tetrahydrofuran; toluene / 0.07 h / -80 °C

4.3: 68 percent / acetic acid / tetrahydrofuran; toluene / -80 - 20 °C

With hydrogen; potassium hexamethylsilazane; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethyl acetate; toluene; acetonitrile;
DOI:10.1002/ejoc.200600154

Reference yield:

: 445483-89-6
(4S)-3-[(4R,2E)-5-tert-butyldiphenylsilyloxy-4-methyl-2-pentenoyl]-4-phenyloxazolidin-2-one

: 445483-91-0
(4S)-3-[(2S,4R)-2-azido-5-tert-butyldiphenylsilyloxy-4-methylpentanoyl]-4-phenyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 100 percent / H₂ / Pd/C / ethyl acetate / 18 h / 20 °C

2.1: KHMDS / tetrahydrofuran; toluene / 0.67 h / -80 °C

2.2: trisyl azide / tetrahydrofuran; toluene / 0.07 h / -80 °C

2.3: 68 percent / acetic acid / tetrahydrofuran; toluene / -80 - 20 °C

With hydrogen; potassium hexamethylsilazane; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; toluene;
DOI:10.1002/ejoc.200600154