58935-95-8Relevant articles and documents
Synthesis of D -Desosamine and Analogs by Rapid Assembly of 3-Amino Sugars
Zhang, Ziyang,Fukuzaki, Takehiro,Myers, Andrew G.
, p. 523 - 527 (2016)
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.
Asymmetric synthesis of congested spiro-cyclopentaneoxindoles via an organocatalytic cascade reaction
Noole, Artur,Ilmarinen, Kaja,Jaerving, Ivar,Lopp, Margus,Kanger, Tonis
, p. 8117 - 8122 (2013/09/12)
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.
Michael additions catalysed by N,N-dimethyl-3-aminopropyl - Derivatised amorphous silica and Hexagonal Mesoporous Silica (HMS)
Mdoe, James E. G.,Clark, James H.,Macquarrie, Duncan J.
, p. 625 - 627 (2007/10/03)
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
