(S)-5-(2-phenyl-ethyl)-4-(N-[allyl]-2-amino-2-methoxycarbonyl-ethyl)-3-izoxazolecarboxylic acid ethyl ester

Base Information

Chemical Name:(S)-5-(2-phenyl-ethyl)-4-(N-[allyl]-2-amino-2-methoxycarbonyl-ethyl)-3-izoxazolecarboxylic acid ethyl ester
CAS No.:691406-73-2
Molecular Formula:C₂₁H₂₆N₂O₅
Molecular Weight:386.448
Hs Code.:

Synonyms:(S)-5-(2-phenyl-ethyl)-4-(N-[allyl]-2-amino-2-methoxycarbonyl-ethyl)-3-izoxazolecarboxylic acid ethyl ester

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Chemical Property of (S)-5-(2-phenyl-ethyl)-4-(N-[allyl]-2-amino-2-methoxycarbonyl-ethyl)-3-izoxazolecarboxylic acid ethyl ester

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Technology Process of (S)-5-(2-phenyl-ethyl)-4-(N-[allyl]-2-amino-2-methoxycarbonyl-ethyl)-3-izoxazolecarboxylic acid ethyl ester

There total 7 articles about (S)-5-(2-phenyl-ethyl)-4-(N-[allyl]-2-amino-2-methoxycarbonyl-ethyl)-3-izoxazolecarboxylic acid ethyl 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:

: 216962-12-8
3-isoxazolecarboxylic acid 5-methyl-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-ethyl ester

: 691406-73-2
(S)-5-(2-phenyl-ethyl)-4-(N-[allyl]-2-amino-2-methoxycarbonyl-ethyl)-3-izoxazolecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.17 h / cooling

1.2: tetrahydrofuran; hexane / 6 h

2.1: 92 percent / p-toluenesulfonic acid monohydrate / acetone

3.1: BF₃*OEt₂ / 0.17 h / cooling

3.2: 68 percent / lead(IV) acetate / benzene

4.1: 54 percent / borane dimethyl sulfide complex / tetrahydrofuran / 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

6.1: toluene / 0.02 h

6.2: L,R,R-Jacobsen peptide / toluene / 49 h / -78 - 20 °C

7.1: hydrogen chloride (gas) / 8 h / 20 °C

With hydrogenchloride; dimethylsulfide borane complex; boron trifluoride diethyl etherate; Dess-Martin periodane; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; acetone; toluene; 5.1: Dess-Martin oxidation / 6.2: Jacobsen-Strecker asymmetric reaction / 7.1: Pinner reaction;
DOI:10.1021/ol049619m

Reference yield:

: 216962-31-1
5-(2-phenyl-ethyl)-4-(methoxycarbonyl)methyl-3-isoxazolecarboxylic acid ethyl ester

: 691406-73-2
(S)-5-(2-phenyl-ethyl)-4-(N-[allyl]-2-amino-2-methoxycarbonyl-ethyl)-3-izoxazolecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 54 percent / borane dimethyl sulfide complex / tetrahydrofuran / 20 °C

2.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

3.1: toluene / 0.02 h

3.2: L,R,R-Jacobsen peptide / toluene / 49 h / -78 - 20 °C

4.1: hydrogen chloride (gas) / 8 h / 20 °C

With hydrogenchloride; dimethylsulfide borane complex; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; toluene; 2.1: Dess-Martin oxidation / 3.2: Jacobsen-Strecker asymmetric reaction / 4.1: Pinner reaction;
DOI:10.1021/ol049619m

Reference yield:

: 216962-29-7
5-(2-phenyl-ethyl)-4-(1-keto-ethyl)-3-isoxazolecarboxylic acid ethyl ester

: 691406-73-2
(S)-5-(2-phenyl-ethyl)-4-(N-[allyl]-2-amino-2-methoxycarbonyl-ethyl)-3-izoxazolecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: BF₃*OEt₂ / 0.17 h / cooling

1.2: 68 percent / lead(IV) acetate / benzene

2.1: 54 percent / borane dimethyl sulfide complex / tetrahydrofuran / 20 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

4.1: toluene / 0.02 h

4.2: L,R,R-Jacobsen peptide / toluene / 49 h / -78 - 20 °C

5.1: hydrogen chloride (gas) / 8 h / 20 °C

With hydrogenchloride; dimethylsulfide borane complex; boron trifluoride diethyl etherate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; toluene; 3.1: Dess-Martin oxidation / 4.2: Jacobsen-Strecker asymmetric reaction / 5.1: Pinner reaction;
DOI:10.1021/ol049619m