(3S,5R)-benzyl-5-[(methoxycarbonyl)methyl]-3-benzyloxycarbonylisooxazolidine-2-carboxylate

Base Information

Chemical Name:(3S,5R)-benzyl-5-[(methoxycarbonyl)methyl]-3-benzyloxycarbonylisooxazolidine-2-carboxylate
CAS No.:1434564-64-3
Molecular Formula:C₂₂H₂₃NO₇
Molecular Weight:413.427
Hs Code.:

Synonyms:(3S,5R)-benzyl-5-[(methoxycarbonyl)methyl]-3-benzyloxycarbonylisooxazolidine-2-carboxylate

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Chemical Property of (3S,5R)-benzyl-5-[(methoxycarbonyl)methyl]-3-benzyloxycarbonylisooxazolidine-2-carboxylate

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Technology Process of (3S,5R)-benzyl-5-[(methoxycarbonyl)methyl]-3-benzyloxycarbonylisooxazolidine-2-carboxylate

There total 8 articles about (3S,5R)-benzyl-5-[(methoxycarbonyl)methyl]-3-benzyloxycarbonylisooxazolidine-2-carboxylate 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: 65.0%

: 1434563-90-2
(2S,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-methylhex-4-enedioate

: 1434564-64-3
(3S,5R)-benzyl-5-[(methoxycarbonyl)methyl]-3-benzyloxycarbonylisooxazolidine-2-carboxylate

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; chloroform; water; at 0 ℃; for 96h;
DOI:10.1021/jo400558t

Reference yield:

: 3426-71-9
Benzyl N-hydroxycarbamate

: 1434564-64-3
(3S,5R)-benzyl-5-[(methoxycarbonyl)methyl]-3-benzyloxycarbonylisooxazolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid / chloroform / 0.17 h / 20 °C

2.2: 3.5 h / 20 °C

3.1: acetic acid; tetrabutyl ammonium fluoride / chloroform; tetrahydrofuran; water / 96 h / 0 °C

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; tetrabutyl ammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; chloroform; water; 3.1: |Michael Addition;
DOI:10.1021/jo400558t

Reference yield:

: 7396-44-3
benzyl diethylphosphonoacetate

: 1434564-64-3
(3S,5R)-benzyl-5-[(methoxycarbonyl)methyl]-3-benzyloxycarbonylisooxazolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: caesium carbonate / cyclohexane / 65 °C

1.2: 2 h / 65 °C

2.1: hydrogenchloride / acetone; water / 48 h / 20 °C

3.1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid / chloroform / 0.17 h / 20 °C

3.2: 3.5 h / 20 °C

4.1: acetic acid; tetrabutyl ammonium fluoride / chloroform; tetrahydrofuran; water / 96 h / 0 °C

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; hydrogenchloride; tetrabutyl ammonium fluoride; caesium carbonate; acetic acid; In tetrahydrofuran; chloroform; cyclohexane; water; acetone; 1.1: |Horner-Wadsworth-Emmons Olefination / 1.2: |Horner-Wadsworth-Emmons Olefination / 4.1: |Michael Addition;
DOI:10.1021/jo400558t