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

Base Information

Chemical Name:(2S,3S)-2-tert-butoxycarbonylamino-5-hydroxy-3-methylpentanoic acid benzyl ester
CAS No.:771578-97-3
Molecular Formula:C₁₈H₂₇NO₅
Molecular Weight:337.416
Hs Code.:

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

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

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

There total 6 articles about (2S,3S)-2-tert-butoxycarbonylamino-5-hydroxy-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:

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

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

Guidance literature:: Multi-step reaction with 7 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

With 4-methyl-morpholine; 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; 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

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

Guidance literature:: Multi-step reaction with 6 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

With 4-methyl-morpholine; 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; water; toluene; acetonitrile; 1.1: Michael reaction;
DOI:10.1016/j.tet.2004.06.111

Reference yield:

: 362660-19-3
(2R,5S,6S)-6-methyl-2-phenyl-1-aza-3-oxabicyclo[3.3.0]octan-8-one

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

Guidance literature:: Multi-step reaction with 5 steps

1.1: 65 percent / NaIO₄ / RuCl₃ / CCl₄; acetonitrile; H₂O / 24 h / 20 °C

2.1: 65 percent / TsOH*H₂O / toluene / 14.5 h / Heating

3.1: 87 percent / DMAP / acetonitrile / 9.5 h / 20 °C

4.1: 91 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

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

5.2: 62 percent / NaBH₄ / 1,2-dimethoxy-ethane; H₂O / 0.17 h / -15 - -10 °C

With 4-methyl-morpholine; dmap; lithium hydroxide; sodium periodate; toluene-4-sulfonic acid; isobutyl chloroformate; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; 1,2-dimethoxyethane; water; toluene; acetonitrile;
DOI:10.1016/j.tet.2004.06.111