30571-61-0Relevant academic research and scientific papers
Regioselective Dehydration of Sugar Thioacetals under Mild Conditions
Szpara, Rachel,Goyder, Alexander,Porter, Michael J.,Hailes, Helen C.,Sheppard, Tom D.
supporting information, p. 2488 - 2492 (2021/04/13)
Sugars are abundant in waste biomass, making them sustainable chiral building blocks for organic synthesis. The demand for chiral saturated heterocyclic rings for pharmaceutical applications is increasing as they provide well-defined three-dimensional frameworks that show increased metabolic resistance. A range of sugar thioacetals can be dehydrated selectively at C-2 under mild basic conditions, and the resulting ketene thioacetals can be applied to the production of useful chiral building blocks via further selective dehydration reactions.
Study of cyclization of diphenylacetals derived from L-rhamnose and L-fucose: A theoretical approach
Banuelos-Hernandez,Mendoza-Espinoza
scheme or table, p. 84 - 90 (2012/08/27)
This work aimed to study the configuration of two mono-tosyl- diphenylacetals, highly flexible molecules derived from L-ramnose and L-fucose, by means of the Monte Carlo conformational search method. The energy of the conformers established by this method and calculated by using the molecular mechanics force field (MMFF) permitted to establish a first conformational space. The geometry of the conformers was optimized by using the semi-empirical AM1 and the density functional B3LYP/DGDZVP methods. We were able to explain the different final products recovered from the reaction of the diphenylacetals derived from L-rhamnose and L-fucose with tosyl chloride, in a pyridine solution. On the other hand, obtaining cyclical compounds by intramolecular cyclization could be an attractive pathway for the synthesis of furanosides.
Conformational analysis of sulfur-containing 6-deoxy-L-hexose derivatives by molecular modeling and NMR spectroscopy. A theoretical study and experimental evidence of intramolecular nonbonded interactions between sulfur and oxygen
Fragoso-Serrano, Mabel,Guillen-Jaramillo, Georgina,Pereda-Miranda, Rogelio,Cerda-Garcia-Rojas, Carlos M.
, p. 7167 - 7175 (2007/10/03)
6-Deoxy-L-mannose diphenyldithioacetal (1) unexpectedly gave the rearranged products phenyl 3,4-di-O-acetyl-2-S-phenyl-1,2-dithio-6-deoxy-β -L-glucopyranoside (9) and 3,4-di-O-acetyl-2,5-anhydro-6-deoxy-L-glucose diphenyldithioacetal (10) upon treatment w
Application of molecular mechanics in the total stereochemical elucidation of spicigerolide, a cytotoxic 6-tetraacetyl-oxyheptenyl-5,6-dihydro-α-pyrone from Hyptis spicigera
Pereda-Miranda, Rogelio,Fragoso-Serrano, Mabel,Cerda-García-Rojas, Carlos M
, p. 47 - 53 (2007/10/03)
Bioactivity-directed fractionation of the crude extract prepared from the medicinal Mexican plant Hyptis spicigera (Lamiaceae) tested on KB cells led to the isolation of spicigerolide (1). The structure for this novel cytotoxic compound was elucidated as
