tert-butyl (R)-2-((4-nitrophenylsulfonyloxy)methyl)aziridine-1-carboxylate

Base Information

Chemical Name:tert-butyl (R)-2-((4-nitrophenylsulfonyloxy)methyl)aziridine-1-carboxylate
CAS No.:1034774-66-7
Molecular Formula:C₁₄H₁₈N₂O₇S
Molecular Weight:358.372
Hs Code.:

Synonyms:tert-butyl (R)-2-((4-nitrophenylsulfonyloxy)methyl)aziridine-1-carboxylate

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Chemical Property of tert-butyl (R)-2-((4-nitrophenylsulfonyloxy)methyl)aziridine-1-carboxylate

Chemical Property:

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Technology Process of tert-butyl (R)-2-((4-nitrophenylsulfonyloxy)methyl)aziridine-1-carboxylate

There total 7 articles about tert-butyl (R)-2-((4-nitrophenylsulfonyloxy)methyl)aziridine-1-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: 82.0%

: tert-butyl (R)-2-(hydroxymethyl)aziridine-1-carboxylate

: 98-74-8
4-Nitrobenzenesulfonyl chloride

: 1034774-66-7
tert-butyl (R)-2-((4-nitrophenylsulfonyloxy)methyl)aziridine-1-carboxylate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 4.5h; stereoselective reaction; Inert atmosphere;
DOI:10.1021/acs.joc.1c00680

Reference yield:

: 2766-43-0
N-tert-butyloxycarbonyl-L-serine methyl ester

: 1034774-66-7
tert-butyl (R)-2-((4-nitrophenylsulfonyloxy)methyl)aziridine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 1H-imidazole / dichloromethane

2: sodium tetrahydroborate; calcium chloride / tetrahydrofuran; ethanol

3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; acetonitrile / 0 - 20 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran; diethyl ether / 0.83 h / 0 °C

5: dmap; triethylamine / dichloromethane / 0 - 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; calcium chloride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetonitrile;
DOI:10.1055/s-0030-1260790

Reference yield:

: 126645-26-9
(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate

: 1034774-66-7
tert-butyl (R)-2-((4-nitrophenylsulfonyloxy)methyl)aziridine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: sodium tetrahydroborate; calcium chloride / tetrahydrofuran; ethanol

2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; acetonitrile / 0 - 20 °C

3: tetrabutyl ammonium fluoride / tetrahydrofuran; diethyl ether / 0.83 h / 0 °C

4: dmap; triethylamine / dichloromethane / 0 - 20 °C

With dmap; sodium tetrahydroborate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; calcium chloride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetonitrile;
DOI:10.1055/s-0030-1260790