58935-95-8

Upstream product

• 6322-49-2 4-chloro-2-butanone 
• 78-94-4 methyl vinyl ketone 
• 75-52-5 nitromethane 

Downstream Products

• 25741-97-3 3-amino-5-methylisoxazole 
• 143957-92-0 (Z)-α-(2-Oxopropyl)-N-benzylnitrone 
• 38572-23-5 (Z)-α-Phenyl-N-(3-oxobutyl)nitrone 

Relevant academic research and scientific papers

Synthesis of D -Desosamine and Analogs by Rapid Assembly of 3-Amino Sugars

D-Desosamine is synthesized in 4 steps from methyl vinyl ketone and sodium nitrite. The key step in this chromatography-free synthesis is the coupling of (R)-4-nitro-2-butanol and glyoxal (trimeric form) mediated by cesium carbonate, which affords in crystalline form 3-nitro-3,4,6-trideoxy-α-D-glucose, a nitro sugar stereochemically homologous to D-desosamine. This strategy has enabled the syntheses of an array of analogous 3-nitro sugars. In each case the 3-nitro sugars are obtained in pure form by crystallization.

SYNTHESIS OF DESOSAMINES

The present invention provides desosamine and mycaminose analogs and nitro sugars and methods for their preparation. The invention also provides methods of cyclizing a compound of Formula (Α') with glyoxal to give a nitro sugar of Formula (B). Methods for the preparation of compound of Formula (D') are provided comprising cyclization of a nitro alcohol to give a nitro sugar and reduction and alkylation of the nitro sugar to give a desosamine, mycaminose, or an analog thereof.

Asymmetric synthesis of congested spiro-cyclopentaneoxindoles via an organocatalytic cascade reaction

Starting from simple alkylidene oxindoles and nitroketones, a highly stereoselective methodology was developed for the synthesis of spiro-cyclopentaneoxindoles with four consecutive stereogenic centers. Using an organocatalytic cascade of Michael and aldol reactions in the presence of a chiral thiourea catalyst products were obtained in moderate to high yields and excellent enantioselectivities. Nitro, ester, and hydroxyl groups were introduced to the spiro ring, which could be used to facilitate further functionalization of the products.

A new strategy for the synthesis of γ-nitro alcohols from aliphatic nitro compounds

A general method for the synthesis of γ-nitro alcohols 1 via C-C-cross-coupling of nitro compounds 3 with silyl derivatives of nitro compounds 4, deoximination of resulting substrates and selective reduction of carbonyl group of ketones 2 is elaborated.

Michael additions catalysed by N,N-dimethyl-3-aminopropyl - Derivatised amorphous silica and Hexagonal Mesoporous Silica (HMS)

Solid bases prepared by derivatisation of amorphous silica and hexagonal mesoporous silica with dimethylaminopropyl groups are good catalysts for Michael addition reactions. Of the prepared catalysts, those based on hexagonal mesoporous silica show partic

Synthesis of analogues of 5-aminolaevulinic acid and inhibition of 5-aminolaevulinic acid dehydratase

Syntheses are described of several analogues of 5-aminolaevulinic acid (ALA), which are potential inhibitors of ALA dehydratase (porphobilinogen synthase), an early enzyme of tetrapyrrole biosynthesis.Most of the analogues are relatively weak competitive inhibitors of the enzyme from Bacillus subtilis or irreversible inhibitors due to multiple alkylation of the enzyme but the 3-oxa and 3-thia analogues are potent mechanism-based inhibitors which inactive, by acylation of a nucleophilic residue, probably the active-site lysine residue.The kinetics of the inactivation by 3-thiaALA have implications for the mechanism of the enzymic reaction.

Assessment of the Active-Site Requirements of 5-Aminolaevulinic Acid Dehydratase: Evaluation of Substrate and Product Analogues as Competitive Inhibitors

The enzyme 5-aminolaevulinic acid dehydratase (ALAD) is resonsible for the synthesis of porphobilinogen (PBG) from two molecules of 5-aminolaevulinic acid (ALA).Porphobilinogen is an important committed intermediate in the biosynthesis of tetrapyrroles.Th

A NEW ROUTE TO 1,4-DIKETONES AND ITS APPLICATION TO (Z)-JASMONE AND DIHYDROJASMONE SYNTHESIS.

(Z)-Jasmone, dihydrojasmone and other 3-methylcyclopent-2-en-1-ones are easily synthetized starting from aldehydes and 1-(2-methyl-1,3-dioxolane-2-yl)-2-nitroethane as reagent for 3-ketobutyl anion synthon.Nitro-aldol condensation is the chainleghtening reaction followed by oxidation and denitration via p-toluenesulfonylhydrazones of the corresponding α-nitroketones.Removal of protecting groups gives 1,4-diketones which are then cyclized with alkali.

A NEW SYNTHESIS OF β-NITRO CARBONYL COMPOUNDS FROM ALKYL VINYL KETONES WITH SODIUM NITRITE-ACETIC ACID IN TETRAHYDROFURAN

The reaction of alkyl vinyl ketones with sodium nitrite-acetic acid in THF gave the corresponding β-nitro carbonyl compounds in 42-82percent yield.

Oxidation products of arachidonic acid. IV. Model studies on the attachment of the C(13)-C(20) side-chain in the synthesis of tetrahydrofurans and pyrans 1, 2, and 3

The synthesis of methyl 15-hydroxy-8(R)-methoxy-11(R)-p-nitrobenzoyloxy-9(S),12(R)-oxy-eicosa-13-ynoate, an arachidonic acid metabolite derivative, is described.As well, methods for the attachment of the C(13)-C(20) prostaglandin side-chain to furanosides were studied and the results are described.The reduction of the C-15 keto group on a model compound was performed and was found to have the same behavior as in the prostaglandins.A partial structure proof of Pace-Asciak's compound, 9,12-oxy-8,11,15-trihydroxy-13-enoic acid is given.