112741-66-9

Upstream product

• 1492-52-0 methyl (S)-2-(benzyloxycarbonlamino)-3-(p-toluenesulfonyl)propionate 
• 501-53-1 benzyl chloroformate 
• 100945-15-1 N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester 
• 181637-35-4 [(1S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-furan-2-yl-3-hydroxy-butyl]-carbamic acid benzyl ester 
• 181637-32-1 N-[(1S,3R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-furan-2-yl-3-hydroxy-butyl]-4-methyl-benzenesulfonamide 
• 181637-29-6 N-((1S,3R)-1-Furan-2-yl-3,4-dihydroxy-butyl)-4-methyl-benzenesulfonamide 
• 148409-93-2 (S)-N-(1-(furan-2-yl)but-3-en-1-yl)-4-methylbenzenesulfonamide 
• 56877-38-4 methyl N-((benzyloxy)carbonyl)-3-iodo-L-alaninate 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 909725-91-3 N-[(diisopropylcarbamoyl)methylene]-4-methoxyaniline N-oxide 
• 107-18-6 allyl alcohol 
• 78553-47-6 methyl (2S)-2-[N-(benzyloxycarbonyl)amino]pent-4-enoate 
• 181637-28-5 ((1S,3R)-1-Furan-2-yl-3,4-dihydroxy-butyl)-carbamic acid benzyl ester 
• 132970-40-2 (S)-2-Benzyloxycarbonylamino-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid methyl ester 

Relevant academic research and scientific papers

Rapid syntheses of 3-amino-5-hydroxymethyl-γ-lactones from L- allylglycine

(3R, 5R) and (3R, 5S) N-protected 3-amino-5-hydroxymethyl-γ-lactones were obtained by one dihydroxylation step from methyl N-protected L- allylglycinate.

Asymmetric 1,3-dipolar cycloaddition of nitrones with an electron-withdrawing group to allylic alcohols utilizing diisopropyl tartrate as a chiral auxiliary

The asymmetric 1,3-dipolar cycloaddition of nitrones possessing an electron-withdrawing group to allylic alcohols was achieved by the use of diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding isoxazolidines with high regio-, diastereo-, and enantioselectivity. In the case of nitrones possessing an electron-withdrawing cyano or t-butoxycarbonyl group, 1,3-dipolar cycloaddition to 2-propen-1-ol occurred to produce the corresponding 3,5-trans-isoxazolidines with high enantioselectivity. To the contrary, nitrones possessing an amide moiety afforded the corresponding optically active 3,5-cis-isoxazolidines with completely opposite diastereoselectivity. A catalytic asymmetric 1,3-dipolar cycloaddition of nitrones possessing the N,N-diisopropylamide moiety to allylic alcohols was achieved to afford di- or trisubstituted isoxazolidines with excellent enantioselectivity of up to over 99% ee. The present asymmetric 1,3-dipolar cycloaddition was applied to the synthesis for the (2S,4R)-4-hydroxyornithine derivative.

Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers

The quorum sensing mechanism in Gram-negative bacteria uses small intercellular signal molecules, N-acyl-homoserine lactones (AHLs), to control transcription of specific genes in relation to population density. In this communication, we describe the parallel synthesis of new AHL analogues, in which substituents have been introduced into the 3- and 4-positions of the lactone ring. These analogues have been screened for their ability to activate and inhibit a Vibrio fischeri LuxI/LuxR-derived quorum sensing reporter system.

A facile transformation of the δ-hydroxy-α-amino lactones from α- furfuryl amide

(S)- and (R)- α- furfuryl amides, obtained from the kinetic resolution of (R, S)- α- furfuryl amide using the modified Sharpless asymmetric epoxidation, have been transformed into four 8-hydroxy α- amino lactones (1S, 3S)-1, (1R, 3R)-1, (1S, 3R)-1, (1R, 3S)-1, using sharpless asymmetric dihydroxylation as the key step. The much more efficient method of the addition of chiral aldimine 10 with allylic Grignard reagent for preparation of (S, S)-1 was also achieved.

A new approach to clavalanine β-lactam antibiotic: Transformation of chiral α-furfuryl amide into the δ-hydroxyl-α-amino lactones via asymmetrical dihydroxylation

Transformation of chiral α-furfuryl amide obtained from kinetic resolution into four δ-hydroxyl-α-amino lactones by utilizing the Sharpless ADH reaction as a key step was achieved.

Amino acids and peptides; 75. Synthesis of di- and trihydroxyamino acids - Construction of lipophilic tripalmitoyldihydroxy-α-amino acids

Suitable protected derivatives of trihydroxynorleucines-[(2S,4S,5S)- and (2R,4S,5S)-2-amino-4,5,6-trihydroxyhexanoic acid], of all isomeric dihydroxynorvalines [2-amino-4,5-dihydroxypentanoic acids), of all isomeric 2-amino-6,7-dihydroxyheptanoic acids an

Practical Asymmetric Syntheses of α-Amino Acids through Carbon-Carbon Bond Constructions on Electrophilic Glycine Templates

The optically active D- and L-erythro-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (3) and D- and L-erythro-4-(tert-butoxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (3) can be efficiently brominated to serve as electrophilic glycine templates for the asymmetric synthesis of amino acids.It was found that coupling to these templates can proceed with either net retention or net inversion of stereochemistry.The final deblocking to the amino acids is accomplished with either dissolving-metal reduction or catalytic hydrogenolysis.The syntheses of β-ethyl aspartic acid, norvaline, allylglycine, alanine, norleucine, homophenylalanine, p-methoxyhomophenylalanine, cyclopentylglycine, and cyclopentenylglycine and a formal synthesis of clavalanine are described.In addition, the direct asymmetric syntheses of N-t-BOC-allylglycine and N-t-BOC-cyclopentenylglycine are described.