95451-97-1Relevant academic research and scientific papers
Building Units of Oligosaccharides, LXXXIII. - Synthesis of the Repeating Unit of the Teichuronic Acid of Micrococcus luteus
Paulsen, Hans,Helpap, Bernd,Lorentzen, Jens Peter
, p. 431 - 438 (2007/10/02)
The disaccharides β-D-ManNAcA-(1--->6)-D-Glc (27) and α-D-Glc-(1--->4)-D-ManNAcA (28) have been synthesized.They represent the repeating unit of the teichuronic acid of Micrococcus luteus.The key steps in the synthesis of the first disaccharide are format
ERPROBTE SYNTHESE VON 2-AZIDO-2-DESOXY-D-MANNOSE UND 2-AZIDO-2-DESOXY-D-MANNURONSAEURE ALS BAUSTEIN ZUM AUFBAU VON BAKTERIEN-POLYSACCHARID-SEQUENZEN
Paulsen, Hans,Lorentzen, Jens Peter,Kutschker, Wolfram
, p. 153 - 176 (2007/10/02)
The azidonitration of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol at low temperature afforded preponderantly the azidonitrate having the D-manno configuration.After reaction with sodium acetate, 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranose was directly isolated and deblocking gave 2-azido-2-deoxy-D-mannopyranose. 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl bromide and 2-azido-3,4,6-tri-O-benzyl-α-D-mannopyranosyl bromide were prepared and are suitable for selective α- and β-glycoside synthesis.In the presence of platinum-oxygen, the catalytic oxidation of benzyl 2-azido-2-deoxy-α-D-mannopyranoside gave in high yields (benzyl 2-azido-2-deoxy-α-D-mannopyranosid)uronic acid from which 2-amino-2-deoxy-D-mannopyranuronic acid was obtained.By catalytic oxidation, selectively blocked derivatives of 2-amino-2-deoxy-D-mannopyranose were converted into the correspondind uronic acid derivatives.
