74342-16-8Relevant academic research and scientific papers
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.
Inhibition of the D-fructose transporter protein GLUT5 by fused-ring glyco-1,3-oxazolidin-2-thiones and -oxazolidin-2-ones
Girniene, Jolanta,Tatibouet, Arnaud,Sackus, Algirdas,Yang, Jing,Holman, Geoffrey D.,Rollin, Patrick
, p. 711 - 719 (2007/10/03)
The glucose transporter 5 (GLUT5) - a specific D-fructose transporter - belongs to a family of facilitating sugar transporters recently enlarged by the human genome sequencing. Prompted by the need to develop specific photolabels of these isoforms, we have studied the interaction of conformationally locked D-fructose and L-sorbose derived 1,3-oxazolidin-2-thiones and 1,3-oxazolidin-2-ones to provide a rational basis for an interaction model. The inhibition properties of the D-fructose transporter GLUT5 by glyco-1,3-oxazolidin-2-thiones and glyco-1,3-oxazolidin-2-ones is now reported. In vitro, the fused-rings systems tested showed an efficient inhibition of GLUT5, thus bringing new insights on the interaction of D-fructose with GLUT5.
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.
A new, stereocontrolled approach to iminosugar C-glycosides from L-sorbose
Masson, Géraldine,Compain, Philippe,Martin, Olivier R.
, p. 2971 - 2974 (2007/10/03)
The efficient synthesis of the iminoalditols derivatives 1 and 2 (nojirimycin α-C-glycosides) has been achieved in 10 steps from commercially available 2,3;4,6-di-O-isopropylidene-α-L-sorbofuranose in an overall yield of 23-27%.
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.
Reactions of Acetals of L-Sorbose with n-Butyllithium
Klemer, Almuth,Jung, Guenter,Meissner, Elke
, p. 1761 - 1767 (2007/10/02)
2,3:4,6-Di-O-isopropylidene-α-L-sorbose (1a) gives with n-butyllithium the known 6-deoxy-2,3-O-isopropylidene-β-D-threo-hex-5-enulofuranose (2), while the corresponding benzylidene compound 4 yields the glycal derivative 2,5-anhydro-4,6-O-benzylidene-3-de
