204577-37-7

Upstream product

• 79-20-9 acetic acid methyl ester 
• 91190-38-4 N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone 
• 141-78-6 ethyl acetate 
• 77086-38-5 ketene t-butyldimethylsilyl methyl acetal 
• 947742-16-7 (S)-5-((2,2-dimethyl-1,3-dioxolan-4-yl)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 622-30-0 N-benzyl hydroxylalmine 
• 2033-24-1 cycl-isopropylidene malonate 
• 29601-98-7 N-benzylhydroxylamine hydrochloride 
• 66601-82-9 methyl (S)-4,5-dihydroxy-4,5-O-isopropylidene-2-pentenoate 

Downstream Products

• 204577-40-2 1-[(3R,5S)-2-Benzyl-3-((S)-1,2-dihydroxy-ethyl)-isoxazolidin-5-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 204577-39-9 Acetic acid (R)-2-benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-isoxazolidin-5-yl ester 
• 204577-38-8 (R)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-isoxazolidin-5-ol 

Relevant academic research and scientific papers

Organocatalyzed Multicomponent Synthesis of Isoxazolidin-5-ones

An unprecedented multicomponent organocatalyzed Knoevenagel-aza-Michael-cyclocondensation reaction between Meldrum's acid, hydroxylamines, and aldehydes afforded a straightforward entry to a large array of racemic and syn-diastereoenriched isoxazolidinone

Organocatalyzed synthesis of isoxazolidin-5-ones: The meldrum's acid approach

Meldrum's acid has turned out to be a useful ketene equivalent when faced to nitrone dipoles to form various isoxazolidin-5-one derivatives under very mild Bronsted base organocatalytic conditions. The first asymmetric version of this original domino anionic formal [3+2] cycloaddition- decarboxylation reaction was demonstrated by means of quinine-based organocatalysts. Copyright

Diastereoselective 1,3-dipolar cycloaddition of ynolates with chiral nitrones

Asymmetric inverse electron-demand 1,3-dipolar cycloaddition of ynolates with chiral nitrones produced 5-isoxazolidinones with good diastereoselectivity. These products were easily converted into optically pure β-amino acids and chiral γ-butyrolactones.

Reaction between N-alkylhydroxylamines and chiral enoate esters: More experimental evidence for a cycloaddition-like process, a rationale based on DFT theoretical calculations, and stereoselective synthesis of new enantiopure β-amino acids

The reactions between N-benzyl- and N-methylhydroxylamine and chiral enoate esters, derived from D-glyceraldehyde and (-)-verbenone, respectively, have been investigated. Theoretical calculations show that the most favorable mechanism involves the concert

Lewis acid stereocontrolled additions of a silyl ketene acetal to 2,3-di-O-isopropylidene-D-glyceraldehyde nitrones. Synthesis of L-isoxazolidinyl nucleosides

The reaction of O-methyl-O-tert-butyldimethylsilyl ketene acetal with N-benzyl and N-methyl-2,3-O-isopropylidene-D-glyceraldehyde nitrones in the presence of boron trifluoride etherate afforded the corresponding isoxazolidin-5-ones in excellent yields and anti-selectivities. The obtained compounds were used as key intermediates for the synthesis of isoxazolidinyl nucleosides of the L-series. (C) 2000 Elsevier Science Ltd.

Modified nucleosides from nitrones: A new and efficient stereoselective approach to isoxazolidinyl thymidine derivatives

The addition of the sodium enolate of methyl acetate to the N-benzyl nitrone 4 derived from D-glyceraldehyde affords the 3-substituted isoxazolidin-5-one 6a with a high degree of syn selectivity and in quantitative chemical yield; its further elaboration