Preparation of methyl 2,3-di-O-mesyl-4,6-thioanhydro-alpha-D-galactopyranoside and methyl 2-O-mesyl-4,6-thioanhydro-alpha-D-gulopyranoside.
Two 2-oxa-7-thiabicyclo[4.2.0]octane derivatives, 4 and 10, with the D-galacto and D-gulo configuration, respectively, were obtained from methyl alpha-D-glucopyranoside. The thietane cyclization involved a thio-Mitsunobu reaction resulting in a 6-thioacetate, which underwent selective base-catalyzed intramolecular nucleophilic substitution at a C-4 mesylate. The structures of 4 and 10 were elucidated by X-ray diffraction analysis.
Adiwidjaja
G
G
Mineralogisch-Petrographisches Institut der Universität Hamburg, Germany.
Brunck
J S
JS
Polchow
K
K
Voss
J
J
D000085:Acetates / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D005690:Galactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D008757:Methylglucosides / Q000737:chemistry*; D008958:Models, Molecular; D009795:Octanes / Q000138:chemical synthesis*; D013696:Temperature; D014961:X-Ray Diffraction
D000085:Acetates; D019086:Bridged Bicyclo Compounds, Heterocyclic; D008757:Methylglucosides; D009795:Octanes; C415343:methyl 2,3-di-O-mesyl-4,6-thioanhydrogalactopyranoside; C415342:methyl 2-O-mesyl-4,6-thioanhydrogulopyranoside; C027020:methylglucoside; C026500:methyl thioacetate; D005690:Galactose