(2S,3S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethylsiloxy)-3-methylpentanoic acid benzyl ester

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Chemical Name:(2S,3S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethylsiloxy)-3-methylpentanoic acid benzyl ester
CAS No.:771578-98-4
Molecular Formula:C₂₄H₄₁NO₅Si
Molecular Weight:451.679
Hs Code.:

Synonyms:(2S,3S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethylsiloxy)-3-methylpentanoic acid benzyl ester

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Chemical Property of (2S,3S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethylsiloxy)-3-methylpentanoic acid benzyl ester

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Technology Process of (2S,3S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethylsiloxy)-3-methylpentanoic acid benzyl ester

There total 8 articles about (2S,3S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethylsiloxy)-3-methylpentanoic 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: 95.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 771578-97-3
(2S,3S)-2-tert-butoxycarbonylamino-5-hydroxy-3-methylpentanoic acid benzyl ester

: 771578-98-4
(2S,3S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethylsiloxy)-3-methylpentanoic acid benzyl ester

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 10.5h;
DOI:10.1016/j.tet.2004.06.111

Reference yield:

: 103201-79-2,1820583-17-2
(3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one

: 771578-98-4
(2S,3S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethylsiloxy)-3-methylpentanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 71 percent / diisopropylamine; n-BuLi; N-tert-butyl benzenesulfinimidoyl chloride / tetrahydrofuran; hexane / -78 - -10 °C

2.1: 86 percent / CuI; Me₃SiCl / tetrahydrofuran; diethyl ether / 1 h / -78 °C

3.1: 65 percent / NaIO₄ / RuCl₃ / CCl₄; acetonitrile; H₂O / 24 h / 20 °C

4.1: 65 percent / TsOH*H₂O / toluene / 14.5 h / Heating

5.1: 87 percent / DMAP / acetonitrile / 9.5 h / 20 °C

6.1: 91 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

7.1: i-BuOCOCl; N-methylmorpholine / 1,2-dimethoxy-ethane / 0.25 h / -15 - -10 °C

7.2: 62 percent / NaBH₄ / 1,2-dimethoxy-ethane; H₂O / 0.17 h / -15 - -10 °C

8.1: 95 percent / imidazole / CH₂Cl₂ / 10.5 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; dmap; lithium hydroxide; sodium periodate; copper(l) iodide; n-butyllithium; chloro-trimethyl-silane; N-tert-butyl benzenesulfinimidoyl chloride; toluene-4-sulfonic acid; diisopropylamine; isobutyl chloroformate; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; 2.1: Michael reaction;
DOI:10.1016/j.tet.2004.06.111

Reference yield:

: 134107-65-6
(3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one

: 771578-98-4
(2S,3S)-2-tert-butoxycarbonylamino-5-(tert-butyldimethylsiloxy)-3-methylpentanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 86 percent / CuI; Me₃SiCl / tetrahydrofuran; diethyl ether / 1 h / -78 °C

2.1: 65 percent / NaIO₄ / RuCl₃ / CCl₄; acetonitrile; H₂O / 24 h / 20 °C

3.1: 65 percent / TsOH*H₂O / toluene / 14.5 h / Heating

4.1: 87 percent / DMAP / acetonitrile / 9.5 h / 20 °C

5.1: 91 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

6.1: i-BuOCOCl; N-methylmorpholine / 1,2-dimethoxy-ethane / 0.25 h / -15 - -10 °C

6.2: 62 percent / NaBH₄ / 1,2-dimethoxy-ethane; H₂O / 0.17 h / -15 - -10 °C

7.1: 95 percent / imidazole / CH₂Cl₂ / 10.5 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; dmap; lithium hydroxide; sodium periodate; copper(l) iodide; chloro-trimethyl-silane; toluene-4-sulfonic acid; isobutyl chloroformate; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; toluene; acetonitrile; 1.1: Michael reaction;
DOI:10.1016/j.tet.2004.06.111