(S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(2-amino-2-methoxycarbonyl-ethyl)-3-isoxazolecarboxylic acid ethyl ester

Base Information

Chemical Name:(S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(2-amino-2-methoxycarbonyl-ethyl)-3-isoxazolecarboxylic acid ethyl ester
CAS No.:691407-11-1
Molecular Formula:C₁₈H₂₂N₂O₆
Molecular Weight:362.382
Hs Code.:

Synonyms:(S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(2-amino-2-methoxycarbonyl-ethyl)-3-isoxazolecarboxylic acid ethyl ester

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Chemical Property of (S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(2-amino-2-methoxycarbonyl-ethyl)-3-isoxazolecarboxylic acid ethyl ester

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Technology Process of (S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(2-amino-2-methoxycarbonyl-ethyl)-3-isoxazolecarboxylic acid ethyl ester

There total 10 articles about (S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(2-amino-2-methoxycarbonyl-ethyl)-3-isoxazolecarboxylic 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:

: 691407-10-0
(S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(N-allyl-2-amino-2-methoxycarbonyl-ethyl)-3-isoxazolecarboxylic acid ethyl ester

: 691407-11-1
(S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(2-amino-2-methoxycarbonyl-ethyl)-3-isoxazolecarboxylic acid ethyl ester

Guidance literature:: With 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; at 35 ℃; for 3h;
DOI:10.1021/ol049619m

Reference yield:

: 646066-64-0
5-[(2,2-ketophenyl)ethyl]-4-(2,5,5-trimethyl-1,3-dioxan-2-yl) 3-isoxazolecarboxylic acid ethyl ester

: 691407-11-1
(S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(2-amino-2-methoxycarbonyl-ethyl)-3-isoxazolecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: (R)-2-methyl-CBS-oxazaborolidine; dimethyl sulfide borane complex / CH₂Cl₂; toluene; tetrahydrofuran / 24 h / -45 °C

2.1: imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

3.1: p-toluenesulfonic acid monohydrate / acetone

4.1: BF₃*OEt₂ / 0.17 h / cooling

4.2: lead(IV) acetate / benzene

5.1: borane dimethyl sulfide complex / tetrahydrofuran / 20 °C

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

7.1: toluene / 0.02 h

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

8.1: hydrogen chloride / 8 h / 20 °C

9.1: N,N'-dimethylbarbituric acid / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / CH₂Cl₂ / 3 h / 35 °C

With 1H-imidazole; hydrogenchloride; dmap; 1,3-dimethylbarbituric acid; dimethylsulfide borane complex; boron trifluoride diethyl etherate; dimethyl sulfide borane; Dess-Martin periodane; toluene-4-sulfonic acid; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; acetone; toluene; 6.1: Dess-Martin oxidation / 7.2: Jacobsen-Strecker reaction;
DOI:10.1021/ol049619m

Reference yield:

: 386707-48-8
3-isoxazolecarboxylic acid 5-[(2,2-hydroxyphenyl)ethyl]-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-ethyl ester

: 691407-11-1
(S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(2-amino-2-methoxycarbonyl-ethyl)-3-isoxazolecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

2.1: (R)-2-methyl-CBS-oxazaborolidine; dimethyl sulfide borane complex / CH₂Cl₂; toluene; tetrahydrofuran / 24 h / -45 °C

3.1: imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

4.1: p-toluenesulfonic acid monohydrate / acetone

5.1: BF₃*OEt₂ / 0.17 h / cooling

5.2: lead(IV) acetate / benzene

6.1: borane dimethyl sulfide complex / tetrahydrofuran / 20 °C

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

8.1: toluene / 0.02 h

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

9.1: hydrogen chloride / 8 h / 20 °C

10.1: N,N'-dimethylbarbituric acid / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / CH₂Cl₂ / 3 h / 35 °C

With 1H-imidazole; hydrogenchloride; dmap; 1,3-dimethylbarbituric acid; dimethylsulfide borane complex; boron trifluoride diethyl etherate; dimethyl sulfide borane; Dess-Martin periodane; toluene-4-sulfonic acid; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; acetone; toluene; 1.1: Dess-Martin oxidation / 7.1: Dess-Martin oxidation / 8.2: Jacobsen-Strecker reaction;
DOI:10.1021/ol049619m