(3R,4’S)-2-N-benzyl-3-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)-1,2-isoxazolidin-5-one

Base Information

• Chemical Name: (3R,4’S)-2-N-benzyl-3-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)-1,2-isoxazolidin-5-one
• CAS No.: 204577-37-7
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.32
• Mol file: 204577-37-7.mol

Synonyms:(3R,4’S)-2-N-benzyl-3-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)-1,2-isoxazolidin-5-one

Chemical Property of (3R,4’S)-2-N-benzyl-3-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)-1,2-isoxazolidin-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4’S)-2-N-benzyl-3-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)-1,2-isoxazolidin-5-one

There total 8 articles about (3R,4’S)-2-N-benzyl-3-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)-1,2-isoxazolidin-5-one 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:

(S)-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (947742-16-7) + N-benzyl hydroxylalmine (622-30-0) → (3S,4’S)-2-N-benzyl-3-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)-1,2-isoxazolidin-5-one (204577-42-4) + (3R,4’S)-2-N-benzyl-3-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)-1,2-isoxazolidin-5-one (204577-37-7)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In ethyl acetate; at 20 ℃; for 14h; diastereoselective reaction;

DOI:10.1021/acs.orglett.5b02755

Reference yield:

N-benzylhydroxylamine hydrochloride (29601-98-7) + methyl (S)-4,5-dihydroxy-4,5-O-isopropylidene-2-pentenoate (66601-82-9) → (3S,4’S)-2-N-benzyl-3-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)-1,2-isoxazolidin-5-one (204577-42-4) + (3R,4’S)-2-N-benzyl-3-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)-1,2-isoxazolidin-5-one (204577-37-7)

Guidance literature:

N-benzylhydroxylamine hydrochloride; methyl (S)-4,5-dihydroxy-4,5-O-isopropylidene-2-pentenoate; With triethylamine; In dichloromethane; at 20 ℃; for 17h;

With silica gel; Further stages.;

DOI:10.1021/jo0159082

Reference yield:

acetic acid methyl ester (79-20-9) + N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4,111058-38-9,1165677-00-8) → (3R,4’S)-2-N-benzyl-3-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)-1,2-isoxazolidin-5-one (204577-37-7)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; Yield given;

DOI:10.1039/a705673g

upstream raw materials:

acetic acid methyl ester

N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone

ethyl acetate

ketene t-butyldimethylsilyl methyl acetal

Downstream raw materials:

(R)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-isoxazolidin-5-ol

Acetic acid (R)-2-benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-isoxazolidin-5-yl ester

1-[(3R,5S)-2-Benzyl-3-((S)-1,2-dihydroxy-ethyl)-isoxazolidin-5-yl]-5-methyl-1H-pyrimidine-2,4-dione