13231-27-1Relevant articles and documents
Mirror-Image Carbohydrates: Synthesis of the Unnatural Enantiomer of a Blood Group Trisaccharide
Boulineau, Fabien P.,Wei, Alexander
, p. 3391 - 3399 (2007/10/03)
Methyl D-glucoside and D-glucose pentaacetate are transformed, respectively, into methyl α-O-glucuronide 3 and hydroxymethyl β-C-glucuronide 9, which undergo decarboxylative elimination efficiently to produce 4-deoxypentenoside 4 and L-glucal 10. These unsaturated pyranosides provide an expeditious entry into mirror-image oligosaccharides, as demonstrated in the synthesis of the unnatural enantiomer of the H-type II blood group determinant trisaccharide (D-Fuc-(α1-2)-L-Gal-(β 1-4)-L-GlcNAc-β-OMe). This work illustrates that D-glucose, a common starting material in the synthesis of naturally occurring carbohydrates, can also be used to prepare their mirror-image analogues.
Studies of the stereoselective reduction of ketosugar (hexosulose)
Chang, Cheng-Wei Tom,Hui, Yu,Elchert, Bryan
, p. 7019 - 7023 (2007/10/03)
The results from the studies of the stereoselective reduction of ketosugar (hexosulose) were reported. Combining our results and those reported in the literature, we summarize the factors in controlling the stereoselective reduction of ketosugars. These findings are valuable in the synthesis of various carbohydrate derivatives.
α-Glucosidase Inhibitors, 3. - 4-Alkylamino-4,6-dideoxy Sugars via Reductive Amination
Koehn, Arnim,Schmidt, Richard R.
, p. 775 - 784 (2007/10/02)
Alkylamino sugars structurally derived from acarbose were obtained by reductive amination of aldehydes or ketones, respectively, and amino sugars mainly with sodium cyanotrihydroborate as reducing agent.Amino sugars investigated were the 4-amino-4,6-dideo