ethyl (2R,3R,4'S)-(+)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-tosylaziridine-2-carboxylate

Base Information

• Chemical Name: ethyl (2R,3R,4'S)-(+)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-tosylaziridine-2-carboxylate
• CAS No.: 240137-04-6
• Molecular Formula: C₁₇H₂₃NO₆S
• Molecular Weight: 369.439

Synonyms:ethyl (2R,3R,4'S)-(+)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-tosylaziridine-2-carboxylate

Chemical Property of ethyl (2R,3R,4'S)-(+)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-tosylaziridine-2-carboxylate

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Technology Process of ethyl (2R,3R,4'S)-(+)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-tosylaziridine-2-carboxylate

There total 1 articles about ethyl (2R,3R,4'S)-(+)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-tosylaziridine-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: 87.0%

p-toluenesulfonylanhydride (4124-41-8) + (2R,3R)-3-[(4S)-(2,2-dimethyl-1,3-dioxolan-4-yl)]-2-ethoxycarbonyl-aziridine (160885-26-7) → ethyl (2S,3S,4'S)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-tosylaziridine-2-carboxylate + ethyl (2R,3R,4'S)-(+)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-tosylaziridine-2-carboxylate (240137-04-6)

Guidance literature:

With dmap; In dichloromethane;

DOI:10.1071/C98026

Reference yield: 87.0%

ethyl (2R,3R,4'S)-(+)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-tosylaziridine-2-carboxylate (240137-04-6) → ethyl (2R,3R,1'S)-(-)-3-(1',2'-dihydroxyethyl)-1-tosylaziridine-2-carboxylate (240137-07-9)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water;

DOI:10.1071/C98026

Reference yield: 51.0%

ethyl (2R,3R,4'S)-(+)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-tosylaziridine-2-carboxylate (240137-04-6) → (2R,3S,4R)-3-hydroxy-4-hydroxymethyl-2-(p-tolylsulfonamido)-4-butanolide (174272-15-2) + (2S,3R,4S)-(+)-2-hydroxy-4-hydroxymethyl-3-tosylaminobutyrolactone

Guidance literature:

With trifluoroacetic anhydride; In 1,4-dioxane; water; at 100 ℃; for 18h;

DOI:10.1071/C98026

upstream raw materials:

p-toluenesulfonylanhydride

(2R,3R)-3-[(4S)-(2,2-dimethyl-1,3-dioxolan-4-yl)]-2-ethoxycarbonyl-aziridine

Downstream raw materials:

(2R,3S,4R)-3-hydroxy-4-hydroxymethyl-2-(p-tolylsulfonamido)-4-butanolide

ethyl (2R,3R,1'S)-(-)-3-(1',2'-dihydroxyethyl)-1-tosylaziridine-2-carboxylate

ethyl (1'S,2R,3R)-(-)-3-<1'-hydroxy-2'-O-mesylethyl>-1-tosylaziridine-2-carboxylate

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