(2R,3R)-N-benzyloxycarbonyl-2-(tert-butoxycarbonyl)-3-methylaziridine

Base Information

• Chemical Name: (2R,3R)-N-benzyloxycarbonyl-2-(tert-butoxycarbonyl)-3-methylaziridine
• CAS No.: 203064-70-4
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.347
• Mol file: 203064-70-4.mol

Synonyms:(2R,3R)-N-benzyloxycarbonyl-2-(tert-butoxycarbonyl)-3-methylaziridine

Chemical Property of (2R,3R)-N-benzyloxycarbonyl-2-(tert-butoxycarbonyl)-3-methylaziridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-N-benzyloxycarbonyl-2-(tert-butoxycarbonyl)-3-methylaziridine

There total 5 articles about (2R,3R)-N-benzyloxycarbonyl-2-(tert-butoxycarbonyl)-3-methylaziridine 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: 80.0%

(2S,3R)-3-Benzyloxycarbonylamino-2-methanesulfonyloxy-butyric acid tert-butyl ester (203064-66-8) → (2R,3R)-N-benzyloxycarbonyl-2-(tert-butoxycarbonyl)-3-methylaziridine (203064-70-4)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1021/jo9720391

Reference yield:

tert-butyl (E)-crotonate (79218-15-8) → (2R,3R)-N-benzyloxycarbonyl-2-(tert-butoxycarbonyl)-3-methylaziridine (203064-70-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / (DHQD)2PHAL; K₂OsO₂(OH)4; t-BuOCl

2: 78 percent / Et₃N / CH₂Cl₂

3: KO-t-Bu

With potassium dioxotetrahydroxoosmate(VI); tert-butylhypochlorite; potassium tert-butylate; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; In dichloromethane;

DOI:10.1016/S0960-894X(03)00666-8

Reference yield:

tert-butyl (2S,3R)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate (203064-64-6) → (2R,3R)-N-benzyloxycarbonyl-2-(tert-butoxycarbonyl)-3-methylaziridine (203064-70-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / Et₃N / CH₂Cl₂

2: KO-t-Bu

With potassium tert-butylate; triethylamine; In dichloromethane;

DOI:10.1016/S0960-894X(03)00666-8

upstream raw materials:

(2S,3R)-3-Benzyloxycarbonylamino-2-methanesulfonyloxy-butyric acid tert-butyl ester

tert-butyl (E)-crotonate

benzyl N-chlorocarbamate

tert-butyl (2S,3R)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate

Downstream raw materials:

(2R,3R)-3-Methyl-1-[4-(2-methyl-benzyloxy)-benzenesulfonyl]-aziridine-2-carboxylic acid tert-butyl ester

(2R,3R)-3-Methyl-1-[4-(2-methyl-pyridin-3-ylmethoxy)-benzenesulfonyl]-aziridine-2-carboxylic acid tert-butyl ester

(2R,3R)-1-[4-(4-Fluoro-benzyloxy)-benzenesulfonyl]-3-methyl-aziridine-2-carboxylic acid tert-butyl ester

(2R,3R)-1-[4-(2-Ethyl-benzyloxy)-benzenesulfonyl]-3-methyl-aziridine-2-carboxylic acid tert-butyl ester