(2S,3S)-2-tert-butoxycarbonylamino-3-methyl-1,5-pentanedioic acid 1-benzyl ester

Base Information

Chemical Name:(2S,3S)-2-tert-butoxycarbonylamino-3-methyl-1,5-pentanedioic acid 1-benzyl ester
CAS No.:771578-96-2
Molecular Formula:C₁₈H₂₅NO₆
Molecular Weight:351.4
Hs Code.:

Synonyms:(2S,3S)-2-tert-butoxycarbonylamino-3-methyl-1,5-pentanedioic acid 1-benzyl ester

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Chemical Property of (2S,3S)-2-tert-butoxycarbonylamino-3-methyl-1,5-pentanedioic acid 1-benzyl ester

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Technology Process of (2S,3S)-2-tert-butoxycarbonylamino-3-methyl-1,5-pentanedioic acid 1-benzyl ester

There total 6 articles about (2S,3S)-2-tert-butoxycarbonylamino-3-methyl-1,5-pentanedioic acid 1-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: 91.0%

: 771578-95-1
(2S,3S)-3-methyl-5-oxopyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester

: 771578-96-2
(2S,3S)-2-tert-butoxycarbonylamino-3-methyl-1,5-pentanedioic acid 1-benzyl ester

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 1h;
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

: 771578-96-2
(2S,3S)-2-tert-butoxycarbonylamino-3-methyl-1,5-pentanedioic acid 1-benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 71 percent / diisopropylamine; n-BuLi; N-tert-butyl benzenesulfinimidoyl chloride / tetrahydrofuran; hexane / -78 - -10 °C

2: 86 percent / CuI; Me₃SiCl / tetrahydrofuran; diethyl ether / 1 h / -78 °C

3: 65 percent / NaIO₄ / RuCl₃ / CCl₄; acetonitrile; H₂O / 24 h / 20 °C

4: 65 percent / TsOH*H₂O / toluene / 14.5 h / Heating

5: 87 percent / DMAP / acetonitrile / 9.5 h / 20 °C

6: 91 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

With dmap; lithium hydroxide; sodium periodate; copper(l) iodide; n-butyllithium; chloro-trimethyl-silane; N-tert-butyl benzenesulfinimidoyl chloride; toluene-4-sulfonic acid; diisopropylamine; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; diethyl ether; hexane; water; toluene; acetonitrile; 2: 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

: 771578-96-2
(2S,3S)-2-tert-butoxycarbonylamino-3-methyl-1,5-pentanedioic acid 1-benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

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

2: 65 percent / NaIO₄ / RuCl₃ / CCl₄; acetonitrile; H₂O / 24 h / 20 °C

3: 65 percent / TsOH*H₂O / toluene / 14.5 h / Heating

4: 87 percent / DMAP / acetonitrile / 9.5 h / 20 °C

5: 91 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

With dmap; lithium hydroxide; sodium periodate; copper(l) iodide; chloro-trimethyl-silane; toluene-4-sulfonic acid; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; diethyl ether; water; toluene; acetonitrile; 1: Michael reaction;
DOI:10.1016/j.tet.2004.06.111