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

Base Information

Chemical Name:(S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(N-allyl-2-amino-2-methoxycarbonyl-ethyl)-3-isoxazolecarboxylic acid ethyl ester
CAS No.:691407-10-0
Molecular Formula:C₂₁H₂₆N₂O₆
Molecular Weight:402.447
Hs Code.:

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

There total 9 articles about (S,S)-5-(2-phenyl-2-hydroxy-ethyl)-4-(N-allyl-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:

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

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

Guidance literature:: Multi-step reaction with 8 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

With 1H-imidazole; hydrogenchloride; dmap; 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; 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

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

Guidance literature:: Multi-step reaction with 9 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

With 1H-imidazole; hydrogenchloride; dmap; 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; In tetrahydrofuran; dichloromethane; acetone; toluene; 1.1: Dess-Martin oxidation / 7.1: Dess-Martin oxidation / 8.2: Jacobsen-Strecker reaction;
DOI:10.1021/ol049619m

Reference yield:

: 691406-98-1
5-(2-phenyl-2-hydroxy-ethyl)-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)-3-isoxazolecarboxylic acid ethyl ester

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

Guidance literature:: Multi-step reaction with 7 steps

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

2.1: p-toluenesulfonic acid monohydrate / acetone

3.1: BF₃*OEt₂ / 0.17 h / cooling

3.2: lead(IV) acetate / benzene

4.1: 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 / 8 h / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; dimethylsulfide borane complex; boron trifluoride diethyl etherate; Dess-Martin periodane; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; acetone; toluene; 5.1: Dess-Martin oxidation / 6.2: Jacobsen-Strecker reaction;
DOI:10.1021/ol049619m