(2S,3S)-2-benzyl-3-((4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-hydroxypropanoic acid

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Chemical Name:(2S,3S)-2-benzyl-3-((4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-hydroxypropanoic acid
CAS No.:1221264-24-9
Molecular Formula:C₂₆H₃₃NO₆
Molecular Weight:455.551
Hs Code.:

Synonyms:(2S,3S)-2-benzyl-3-((4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-hydroxypropanoic acid

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Chemical Property of (2S,3S)-2-benzyl-3-((4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-hydroxypropanoic acid

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Technology Process of (2S,3S)-2-benzyl-3-((4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-hydroxypropanoic acid

There total 9 articles about (2S,3S)-2-benzyl-3-((4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-hydroxypropanoic acid 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: 67.0%

: 1221264-23-8
(4R)-tert-butyl 2-((1S,2S)-2-benzyl-1-hydroxy-3-((S)-4-isopropyl-2-oxooxazolidin-3-yl)-3-oxopropyl)-4-(benzyloxy)pyrrolidine-1-carboxylate

: 1221264-24-9
(2S,3S)-2-benzyl-3-((4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-hydroxypropanoic acid

Guidance literature:: (4R)-tert-butyl 2-((1S,2S)-2-benzyl-1-hydroxy-3-((S)-4-isopropyl-2-oxooxazolidin-3-yl)-3-oxopropyl)-4-(benzyloxy)pyrrolidine-1-carboxylate; With lithium hydroxide monohydrate; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃;

With sodium sulfite; In tetrahydrofuran; water; at 0 ℃; for 0.5h;

With hydrogenchloride; In tetrahydrofuran; water; pH=2;

Reference yield:

: 114676-59-4
(2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride

: 1221264-24-9
(2S,3S)-2-benzyl-3-((4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-hydroxypropanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: dmap; triethylamine / water; acetone

2.1: silver(l) oxide / N,N-dimethyl-formamide / 36 h / 0 °C

3.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C

3.2: 0 °C / pH 4

4.1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 0.5 h / 0 - 20 °C

5.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

5.2: -78 - 20 °C / Inert atmosphere

5.3: 1 h / 0 °C / Aqueous phosphate buffer

6.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 °C

6.2: 0.5 h / 0 °C

6.3: pH 2

With dmap; lithium borohydride; lithium hydroxide monohydrate; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; sulfur trioxide pyridine complex; triethylamine; N-ethyl-N,N-diisopropylamine; silver(l) oxide; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

Reference yield:

: 114676-69-6
(2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

: 1221264-24-9
(2S,3S)-2-benzyl-3-((4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-hydroxypropanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: silver(l) oxide / N,N-dimethyl-formamide / 36 h / 0 °C

2.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C

2.2: 0 °C / pH 4

3.1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 0.5 h / 0 - 20 °C

4.1: di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

4.3: 1 h / 0 °C / Aqueous phosphate buffer

5.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 °C

5.2: 0.5 h / 0 °C

5.3: pH 2

With lithium borohydride; lithium hydroxide monohydrate; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; sulfur trioxide pyridine complex; triethylamine; N-ethyl-N,N-diisopropylamine; silver(l) oxide; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;