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.
Synthesis of analogues of 5-aminolaevulinic acid and inhibition of 5-aminolaevulinic acid dehydratase
Appleton, Diana,Duguid, A. Bruce,Lee, Sung-Koo,Ha, Young-Jin,Ha, Hyun-Joon,Leeper, Finian J.
, p. 89 - 102 (2007/10/03)
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.