Synthesis, crystal structure, and high-resolution NMR spectroscopy of methyl 3-azido-2,3-dideoxy-4,6-di-O-p-tolylsulfonyl-alpha-D-xylo-hexopyranoside.
Synthesis of methyl 3-azido-2,3-dideoxy-4,6-di-O-p-tolylsulfonyl- and -6-O-p-tolylsulfonyl-alpha-D-xylo-hexopyranosides is presented. High-resolution 1H and 13C NMR spectral data for both compounds and their precursors, and the single-crystal X-ray diffraction analysis for methyl 3-azido-2,3-dideoxy-4,6-di-O-p-tolylsulfonyl-alpha-D-xylo-hexopyranoside are reported. The influence of the O-protective group on the chemical shift of adjacent atoms in the 1H and 13C NMR spectra is discussed.
Liberek
Beata
B
Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, PL-80-952 Gdańsk, Poland. beatal@chemik.chem.univ.gda.pl
Sikorski
Artur
A
Konitz
Antoni
A
D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry*; D002236:Carbohydrate Conformation; D003460:Crystallization; D018360:Crystallography, X-Ray; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D014961:X-Ray Diffraction
D001386:Azides; D006027:Glycosides; C502288:methyl 3-azido-2,3-dideoxy-4,6-di-O-4-tolylsulfonylhexopyranoside