Synthesis, the crystal structure, and high-resolution NMR spectroscopy of methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-6-iodo-alpha-D-arabino-hexopyranoside.
Selective tosylation followed by acetylation of methyl 3-azido-2,3-dideoxy-alpha-D-arabino-hexopyranoside (1) in pyridine at room temperature affords a mixture of methyl 4-O-acetyl-3-azido-2,3-dideoxy-6-di-O-p-tolylsulfonyl-alpha-D-arabino-hexopyranoside (4) and methyl 3-azido-2,3-dideoxy-4,6-di-O-p-tolylsulfonyl-alpha-D-arabino-hexopyranoside (3). Compound 4 undergoes nucleophilic displacement with sodium iodide in acetic anhydride to give methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-6-iodo-alpha-D-arabino-hexopyranoside (7), whose crystal structure and (1H) and (13)C NMR data are reported. This compound adopts the 4C(1) conformation.
Dabrowska
Aleksandra
A
Department of Chemistry, University of Gdańsk, 18/19 Sobieski Strasse, PL-80-952 Gdańsk, Poland. alex@chemik.chem.univ.gda.pl
Konitz
Antoni
A
Smiatacz
Zygfryd
Z
D001089:Arabinose / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry*; D003460:Crystallization; D003837:Deoxy Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure; D014961:X-Ray Diffraction / Q000379:methods
D001386:Azides; D003837:Deoxy Sugars; C456721:methyl-4-O-acetyl-3-azido-2,3,6-trideoxy-6-iodo-arabino-hexopyranoside; D001089:Arabinose