(2R,3R,4S)-1-benzyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-aziridine-2-carboxylic acid ethyl ester

Base Information

• Chemical Name: (2R,3R,4S)-1-benzyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-aziridine-2-carboxylic acid ethyl ester
• CAS No.: 160885-25-6
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374
• Mol file: 160885-25-6.mol

Synonyms:(2R,3R,4S)-1-benzyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-aziridine-2-carboxylic acid ethyl ester

Chemical Property of (2R,3R,4S)-1-benzyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-aziridine-2-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S)-1-benzyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-aziridine-2-carboxylic acid ethyl ester

There total 4 articles about (2R,3R,4S)-1-benzyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-aziridine-2-carboxylic 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: 68.0%

(Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-bromo-2-propenoate (182969-96-6) + benzylamine (100-46-9) → (2R,3R,4S)-1-benzyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-aziridine-2-carboxylic acid ethyl ester (160885-25-6) + (2S,3R,4S)-(-)-1-Benzyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)aziridin-2-carbonsaeure-ethylester (161904-73-0)

Guidance literature:

With triethylamine; In toluene; at 20 ℃; for 24h; Overall yield = 75 %; Cooling;

DOI:10.1039/c5ra06429e

Reference yield:

2,3-isopropylidene-glyceraldehyde (15186-48-8) → (2R,3R,4S)-1-benzyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-aziridine-2-carboxylic acid ethyl ester (160885-25-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / CH₂Cl₂ / 1 h / Ambient temperature

2: 40 percent / NEt₃ / ethanol / 72 h / Ambient temperature

With triethylamine; In ethanol; dichloromethane;

Reference yield:

1,2:5,6-di-O-isopropylidene-D-mannitol (1707-77-3) → (2R,3R,4S)-1-benzyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-aziridine-2-carboxylic acid ethyl ester (160885-25-6) + (2S,3R,4S)-(-)-1-Benzyl-3-(2,2-dimethyl-1,3-dioxolan-4-yl)aziridin-2-carbonsaeure-ethylester (161904-73-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium periodate; sodium hydrogencarbonate / dichloromethane; water / 35 °C / Cooling

2: dichloromethane / 1 h / 20 °C

3: triethylamine / toluene / 24 h / -5 - 20 °C

With sodium periodate; sodium hydrogencarbonate; triethylamine; In dichloromethane; water; toluene;

DOI:10.1016/j.tetlet.2021.153119

upstream raw materials:

(Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-bromo-2-propenoate

benzylamine

2,3-isopropylidene-glyceraldehyde

1,2:5,6-di-O-isopropylidene-D-mannitol

Downstream raw materials:

(2R)-piperidin-2-ylmethanol

(2R,3R)-3-hydroxypipecolic acid

(R)-(+)-pipecolic acid