74342-16-8Relevant articles and documents
Selective protecting group manipulations on the 1-deoxynojirimycin scaffold
Danieli, Elisa,Lalot, Jér?me,Murphy, Paul V.
, p. 6827 - 6834 (2007)
Iminosugars are inhibitors of glycoprocessing and are of interest as scaffolds for medicinal chemistry, as their successful application as peptide mimetics has shown. The synthesis of novel peptidomimetics based on 1-deoxynojirimycin (DNJ) requires practical strategies that allow introduction of amino acid side chains or pharmacophore groups at each of its hydroxyl groups or to the nitrogen atom. This paper describes one approach towards achieving selective protection and deprotection at the hydroxyl and amino groups of?DNJ and a novel synthesis of DNJ from l-sorbose is included.
A general strategy for the practical synthesis of nojirimycin C-glycosides and analogues. Extension to the first reported example of an iminosugar 1-phosphonate
Godin, Guillaume,Compain, Philippe,Masson, Geraldine,Martin, Olivier R.
, p. 6960 - 6970 (2007/10/03)
An efficient and versatile strategy for the synthesis of nojirimycin C-glycosides and related compounds with full stereocontrol is reported. The key steps of the process are the addition of organometallic reagents onto an L-sorbose-derived imine (13) followed by an internal reductive amination. The addition step, which controls the α vs β-configuration at the pseudoanomeric center in the final product, is highly diastereoselective (re-face addition), and the stereoselectivity can be effectively inverted by adding an external monodentate Lewis acid (si-face addition). The complete synthesis could be achieved in 10 steps only from commercially available 2,3;4,6-di-O-isopropylidene-C-L-sorbofuranose and provided α or β-1-C-substituted 1-deoxynojirimycin derivatives in 27-52% overall yield. The strategy was successfully extended to the first example of an iminosugar 1-phosphonate. The methodology provides access to a wide range of biologically relevant glycoconjugate mimetics in which the glycosidic function is replaced by an imino-C-glycosidic linkage.
Synthesis of a mixture of (2S,5R)- and (2S,5S)-2-methyl-1,6-dioxaspiro[4.5]decane, the odor bouquet minor components of Paravespula vulgaris (L.), from L-sorbose
Izquierdo Cubero,Lopez-Espinosa,Kari
, p. 187 - 200 (2007/10/02)
The synthesis of (2S,5RS)-2-methyl-1,6-dioxaspiro[4.5]decane (1) from (2S,4S,5R)- (26) and (2S,4S,5S)-4-hydroxy-2-methyl-1,6-dioxaspiro[4.5]decane (27), obtained in thirteen and fourteen steps from L-sorbose by two convergent syntheses, has been accomplished using Wittig methodology, Barton deoxygenation, reduction, and spiroketalation of the appropriately protected derivatives.
