105017-72-9Relevant academic research and scientific papers
Synthesis and conformational analysis of carbasugar bioisosteres of α-l-iduronic acid and its methyl glycoside
S?wén, Elin,Roslund, Mattias U.,Cumpstey, Ian,Widmalm, G?ran
experimental part, p. 984 - 993 (2010/08/20)
The synthesis of two novel carbasugar analogues of α-l-iduronic acid is described in which the ring-oxygen is replaced by a methylene group. In analogy with the conformational equilibrium described for α-l-IdopA, the conformation of the carbasugars was investigated by 1H and 13C NMR spectroscopy. Hadamard transform NMR experiments were utilised for rapid acquisition of 1H,13C-HSQC spectra and efficient measurements of heteronuclear long-range coupling constants. Analysis of 1H NMR chemical shifts and JH,H coupling constants extracted by a total-lineshape fitting procedure in conjunction with JH,C coupling constants obtained by three different 2D NMR experiments, viz., 1H,13C-HSQC-HECADE, J-HMBC and IPAP-HSQC-TOCSY-HT, as well as effective proton-proton distances from 1D 1H,1H T-ROE and NOE experiments showed that the conformational equilibrium 4C1?2S5a?1C4 is shifted towards 4C1 as the predominant or exclusive conformation. These carbasugar bioisosteres of α-l-iduronic acid do not as monomers show the inherent flexibility that is anticipated to be necessary for biological activity.
Cyclitol Reactions, XIII.- Synthesis of Pseudosugars from D-Glucose by Intramolecular Horner-Emmons Olefination
Paulsen, Hans,Deyn, Wolfgang von
, p. 125 - 131 (2007/10/02)
The reaction of the aldehyde 3, prepared from D-glucose diethyl dithioacetal via 1 and 2, with lithium dimethyl methylphosphonat yields the adduct 4.Conversion of 4 into 9 followed by Swern oxidation results in the enone 6.Hydrogenation of 6 leads to pseu
