ethyl (2S,3S,4R,5S)-1-benzyl-3,4-isopropylidenedioxy-5-methylpyrrolidine-2-acetate

Base Information

• Chemical Name: ethyl (2S,3S,4R,5S)-1-benzyl-3,4-isopropylidenedioxy-5-methylpyrrolidine-2-acetate
• CAS No.: 1314088-78-2
• Molecular Formula: C₁₉H₂₇NO₄
• Molecular Weight: 333.428
• Mol file: 1314088-78-2.mol

Synonyms:ethyl (2S,3S,4R,5S)-1-benzyl-3,4-isopropylidenedioxy-5-methylpyrrolidine-2-acetate

Chemical Property of ethyl (2S,3S,4R,5S)-1-benzyl-3,4-isopropylidenedioxy-5-methylpyrrolidine-2-acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2S,3S,4R,5S)-1-benzyl-3,4-isopropylidenedioxy-5-methylpyrrolidine-2-acetate

There total 8 articles about ethyl (2S,3S,4R,5S)-1-benzyl-3,4-isopropylidenedioxy-5-methylpyrrolidine-2-acetate 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: 35.0%

(2S,3aS,4S,5R,6S)-2-ethyloxy-4,5-isopropylidenedioxy-6-methylhexahydropyrrolo[1,2-b]isoxazole (1314088-77-1) + benzyl bromide (100-39-0) → ethyl (2S,3S,4R,5S)-1-benzyl-3,4-isopropylidenedioxy-5-methylpyrrolidine-2-acetate (1314088-78-2)

Guidance literature:

In 1,1,2,2-tetrachloroethane; at 50 ℃; for 24h;

DOI:10.1016/j.carres.2011.03.030

Reference yield:

5-deoxy-2,3-O-isopropylidene-4-O-methanesulfonyl-D-ribose O-(tert-butyl-dimethyl)silyl oxime → ethyl (2S,3S,4R,5S)-1-benzyl-3,4-isopropylidenedioxy-5-methylpyrrolidine-2-acetate (1314088-78-2)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrabutyl ammonium fluoride; triethylamine / acetonitrile / 6 h / 80 °C

2: 1,1,2,2-tetrachloroethane / 16 h / 50 °C

3: 1,1,2,2-tetrachloroethane / 24 h / 50 °C

With tetrabutyl ammonium fluoride; triethylamine; In acetonitrile; 1,1,2,2-tetrachloroethane;

DOI:10.1016/j.carres.2011.03.030

Reference yield:

5-deoxy-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-D-ribitol (1314088-68-0) → ethyl (2S,3S,4R,5S)-1-benzyl-3,4-isopropylidenedioxy-5-methylpyrrolidine-2-acetate (1314088-78-2)

Guidance literature:

Multi-step reaction with 4 steps

1: hydroxylamine hydrochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine / 85 °C

2: mercury(II) oxide / 6 h / 20 °C

3: 1,1,2,2-tetrachloroethane / 16 h / 50 °C

4: 1,1,2,2-tetrachloroethane / 24 h / 50 °C

With hydroxylamine hydrochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; mercury(II) oxide; In 1,1,2,2-tetrachloroethane;

DOI:10.1016/j.carres.2011.03.030

upstream raw materials:

5-deoxy-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-D-ribitol

1,4,5-trideoxy-N-hydroxy-1,4-imino-2,3-O-isopropylidene-L-lyxitol

(2S,3aS,4S,5R,6S)-2-ethyloxy-4,5-isopropylidenedioxy-6-methylhexahydropyrrolo[1,2-b]isoxazole

benzyl bromide